[Federal Register Volume 64, Number 84 (Monday, May 3, 1999)]
[Proposed Rules]
[Pages 23554-23570]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 99-10818]


=======================================================================
-----------------------------------------------------------------------

DEPARTMENT OF THE TREASURY

Internal Revenue Service

26 CFR Part 1

[REG-106004-98]
RIN 1545-AW71


Guidance Under Section 355(d); Recognition of Gain on Certain 
Distributions of Stock or Securities

AGENCY: Internal Revenue Service (IRS), Treasury.

ACTION: Notice of proposed rulemaking and notice of public hearing.

-----------------------------------------------------------------------

SUMMARY: This document contains proposed regulations relating to 
recognition of gain on certain distributions of stock or securities of 
a controlled corporation. These proposed regulations affect 
corporations and their shareholders. Proposed regulations are necessary 
because of statutory changes made by the Omnibus Budget Reconciliation 
Act of 1990. This document also provides notice of a public hearing on 
these proposed regulations.

DATES: Written and electronic comments must be received by August 2, 
1999. Outlines of topics to be discussed at the public hearing 
scheduled for September 21, 1999, at 10 a.m. must be received by August 
31, 1999.

ADDRESSES: Send submissions to CC:DOM:CORP:R (REG-106004-98), room 
5226, Internal Revenue Service, POB 7604, Ben Franklin Station, 
Washington, DC 20044. Submissions may be hand delivered Monday through 
Friday between the hours of 8 a.m. and 5 p.m. to: CC:DOM:CORP:R (REG-
106004-98), Courier's Desk, Internal Revenue Service, 1111 Constitution 
Avenue, NW., Washington, DC. Alternatively, taxpayers may submit 
comments electronically via the Internet by selecting the ``Tax Regs'' 
option on the IRS Home Page, or by submitting comments directly to the 
IRS Internet site at http://www.irs.ustreas.gov/tax__regs/
regslist.html. The public hearing will be held in room 2615, Internal 
Revenue Building, 1111 Constitution Avenue, N.W., Washington, DC.

FOR FURTHER INFORMATION CONTACT: Concerning the proposed regulations, 
Robert Hawkes (202) 622-7530 or Phoebe Bennett (202) 622-7750; 
concerning submissions of comments, the hearing, and/or to be placed on 
the building access list to attend the hearing, Guy R. Traynor (202) 
622-7190 (not toll-free numbers).

SUPPLEMENTARY INFORMATION:

Background

    If the requirements of section 355(a) are met, a distributing 
corporation (Distributing) may distribute the stock or securities of a 
controlled corporation (Controlled) to its shareholders or security 
holders (Distributees) with no gain or loss recognized to the 
Distributees. A Distributee allocates its basis in Distributing stock 
or securities between the Controlled stock or securities received in 
the distribution and any Distributing stock or securities retained in 
proportion to the fair market value of each. See section 358; 
Secs. 1.358-1 and 1.358-2. If neither section 355 (d) nor (e) applies, 
then Distributing generally recognizes no gain on the distribution of 
stock or securities. See section 355(c)(2) or 361(c)(2).
    With limited exceptions, the Tax Reform Act of 1986 (Public Law 99-
514, 100 Stat. 208) (TRA), repealed the doctrine of General Utilities & 
Operating Co. v. Helvering, 296 U.S. 200 (1935), by requiring a 
corporation to recognize gain on both liquidating and nonliquidating 
distributions of appreciated property. In retaining section 355 as an 
exception to General Utilities repeal, Congress intended to permit 
historic shareholders to carry on their historic corporate businesses 
in separate corporations. See H. R. Rep. 101-881, at 341 (1990). 
However, Congress became concerned that, after the TRA, a person could 
purchase a historic shareholder's

[[Page 23555]]

interest, receive a distribution of Controlled stock tax-free to both 
Distributing and the purchaser, and obtain a fair market value basis in 
the Controlled stock. Accordingly, Congress amended section 
355(b)(2)(D) in the Omnibus Budget Reconciliation Act of 1987 (Public 
Law 100-203, section 10223, 101 Stat. 1330-411) (1987 OBRA) to make 
section 355 inapplicable where a Distributee acquired control (as 
defined in section 368(c)) of a corporation conducting a business in a 
taxable transaction during the five-year period ending on the date of 
the distribution. See H. R. Rep. No. 100-391, at 1082-83 (1987). 
However, section 355(b)(2)(D) did not apply to noncorporate purchasers 
or purchasers of less than 80 percent of Distributing stock.
    Section 355(d), enacted as part of the Omnibus Budget 
Reconciliation Act of 1990 (Public Law 101-508, section 11321(a), 104 
Stat. 1388-460) (1990 OBRA), followed the purposes of the 1987 OBRA 
provisions but substantially expanded their scope. See H. R. Rep. 101-
881, at 341 (1990). In section 355(d), Congress intended to prevent the 
use of section 355 either to ``dispose of subsidiaries in transactions 
that resemble sales, or to obtain a fair market value stepped-up basis 
for any future dispositions, without incurring corporate-level tax.'' 
Id.
    Section 355(d) requires recognition of gain on a distribution of 
Controlled stock (as though the Controlled stock were sold to the 
Distributee at its fair market value) if, immediately after the 
distribution, any person holds disqualified stock of Distributing or 
any distributed Controlled that constitutes a 50 percent or greater 
interest. See section 355(d) (1) and (2). Disqualified stock is stock 
in Distributing acquired by purchase after October 9, 1990 and during 
the five-year period (taking into account section 355(d)(6)) ending on 
the date of distribution (the five-year period), or Controlled stock 
either (1) acquired by purchase during the five-year period or (2) 
distributed with respect to either disqualified Distributing stock or 
on Distributing securities acquired by purchase during the five-year 
period. See section 355(d)(3). A 50 percent or greater interest means 
stock possessing at least 50 percent of the total combined voting power 
of all classes of stock entitled to vote or at least 50 percent of the 
total value of shares of all classes of stock. See section 355(d)(4). 
Section 355(d) also contains a definition of purchase (section 
355(d)(5)), a provision suspending the five-year period for certain 
stock or securities (section 355(d)(6)), and aggregation and 
attribution provisions (section 355(d) (7) and (8)). Section 355(d)(9) 
authorizes regulations to carry out the purposes of section 355(d), 
including regulations to prevent the avoidance of its purposes through 
the use of related persons, intermediaries, pass-through entities, 
options, or other arrangements, and regulations modifying the 
definition of purchase.

Explanation of Provisions

(a) General Rules and Purposes of Section 355(d)

    As stated above, section 355(d) is intended to prevent taxpayers 
from using section 355 to dispose of subsidiaries in sale-like 
transactions, or to obtain a fair market value stepped-up basis for 
future dispositions, without incurring a corporate-level tax. See H. R. 
Rep. 101-881, at 341 (1990). The legislative history to section 355(d) 
describes transactions generally not violating the purposes of section 
355(d):

    The purposes of [section 355(d)] are not generally violated if 
there is a distribution of a controlled corporation within 5 years 
of an acquisition by purchase and the effect of the distribution is 
neither (1) to increase ownership in the distributing corporation or 
any controlled corporation by persons who have directly or 
indirectly acquired stock within the prior five years, nor (2) to 
provide a basis step-up with respect to the stock of any controlled 
corporation.

H. R. Rep. No. 101-964 (Conference Report), at 1093 (1990).
    The Conference Report, at page 1091, clarifies that the grant of 
regulatory authority in section 355(d)(9) includes the authority to 
exclude from section 355(d) transactions not violating its purposes. 
The proposed regulations provide that a distribution is not a 
disqualified distribution under section 355(d)(2) and proposed 
Sec. 1.355-6(b)(1) if the distribution and any related transactions do 
not violate the purposes of section 355(d). The proposed regulations 
describe transactions not violating the purposes of section 355(d) in a 
manner similar to the legislative history and provide some examples of 
those transactions. If a distribution does not violate the purposes of 
section 355(d) under proposed Sec. 1.355-6(b)(3), such distribution is 
a distribution to which section 355(d) does not apply. Accordingly, 
such a distribution still could be a distribution to which section 
355(e) applies. See section 355(e)(2)(D).
    The exception in the proposed regulations for transactions that do 
not violate the purposes of section 355(d) applies to transactions in 
which a disqualified person neither increases an interest nor obtains a 
purchased basis in Controlled stock. A disqualified person is any 
person that, immediately after a distribution, holds disqualified stock 
in Distributing or Controlled that constitutes a 50-percent or greater 
interest (under section 355(d)(4) and proposed Sec. 1.355-6(c)). Based 
on examples in the Conference Report, the proposed regulations define 
purchased basis as basis in Controlled stock that is disqualified 
stock, unless the Controlled stock and the Distributing stock on which 
the Controlled stock is distributed are treated as acquired by purchase 
solely under the attribution rules of section 355(d)(8) and proposed 
Sec. 1.355-6(e)(1). Examples in the proposed regulations demonstrate 
the application of the two-pronged purpose test.
    The proposed regulations also provide that a person that acquires 
an interest in any entity by purchase is not treated as having acquired 
by purchase stock owned by the entity under section 355(d)(8)(B) and 
paragraph (e)(1) of this section when the person no longer holds the 
directly purchased interest. Examples demonstrate the operation of this 
rule when purchased stock is eliminated in a liquidation or upstream 
merger.
    The proposed regulations provide an anti-avoidance rule that 
permits the Commissioner to treat any distribution as a disqualified 
distribution under section 355(d)(2) and proposed Sec. 1.355-6(b)(1) if 
the distribution or another transaction or transactions are engaged in 
or structured with a principal purpose to avoid the purposes of section 
355(d) or the regulations thereunder with respect to the distribution. 
For example, the Commissioner may determine that the existence of a 
related person, intermediary, pass-through entity, or similar person 
(an intermediary) should be disregarded, in whole or in part, if the 
intermediary is formed or availed of with a principal purpose to avoid 
the purposes of section 355(d) or the regulations thereunder.

(b) Whether a Person Holds a 50 Percent or Greater Interest

    Under section 355(d)(4), 50 percent or greater interest means stock 
possessing at least 50 percent of the total combined voting power of 
all classes of stock entitled to vote or at least 50 percent of the 
total value of shares of all classes of stock. The proposed regulations 
provide rules relating to that definition.

Valuation

    The proposed regulations provide that, for purposes of section 
355(d)(4) and proposed Sec. 1.355-6, all shares of stock within a 
single class are

[[Page 23556]]

considered to have the same value. But see proposed Sec. 1.355-
6(c)(3)(vii), which applies a special valuation rule to determine 
whether options are reasonably certain to be exercised.
Effect of Options, Warrants, Convertible Obligations, and Other Similar 
Interests
    Section 355(d)(9) provides regulatory authority to prevent the 
avoidance of the purposes of section 355(d) through the use of options. 
The Conference Report states, at page 1092, that Congress intends that 
regulations be issued to treat an option to acquire stock as exercised 
if two criteria are satisfied. The first is that a deemed exercise 
would cause a person to have a 50 percent or greater interest acquired 
by purchase. The second is that, under all the facts and circumstances 
(including projected earnings or appreciation and including the risk 
shifting or other effects of any other arrangements with the option 
holder or related parties), the effect of the option would be to avoid 
the application of section 355(d).
    In general, the proposed regulations disregard options in 
determining whether any person holds disqualified stock constituting a 
50 percent or greater interest. However, under the proposed 
regulations, an option to acquire stock that has not been exercised 
when a distribution occurs is treated as exercised on the date it was 
issued or most recently transferred if two criteria are satisfied. The 
first, based on the Conference Report, is that a deemed exercise would 
cause a person to become a disqualified person. An option is not 
treated as exercised under this criterion, however, if the effect of 
the treatment is to prevent a person who would otherwise be a 
disqualified person from being treated as a disqualified person. The 
second criterion is that, immediately after the distribution of 
Controlled, and based on all the facts and circumstances, it is 
reasonably certain that the option will be exercised. The IRS and 
Treasury believe that the proposed regulations, which employ a 
``reasonably certain'' standard to treat options as exercised in 
potentially abusive situations, is consistent with the guidance given 
in the Conference Report with respect to options. The proposed 
regulations generally except certain instruments not ordinarily having 
an abuse potential from treatment as options, such as escrow, pledge, 
or other security agreements, compensatory options, and options 
exercisable only upon death, disability, mental incompetency, or 
retirement.
    When an option is treated as exercised, it is treated as exercised 
both for purposes of determining the percentage of the voting power of 
stock owned and for purposes of determining the percentage of the value 
of stock owned. The effect of control premiums and minority and 
blockage discounts on stock value is taken into account only for 
purposes of applying the ``reasonably certain'' test. If the 
``reasonably certain'' test is met, so that an option is treated as 
exercised, all shares of a single class are considered to have the same 
value for purposes of determining the amount of stock deemed acquired 
under the option.
    The option rules of proposed Sec. 1.355-6(c)(3) determine when an 
option is treated as exercised only for purposes of section 355(d) (but 
not for purposes of section 355(d)(6)) and do not apply for purposes of 
any other sections of the Internal Revenue Code. The option rules are 
proposed to apply generally to options outstanding in distributions 
occurring after the regulations are published as final regulations in 
the Federal Register. See proposed Sec. 1.355-6(g). However, the 
Service may apply substance over form principles in determining whether 
options outstanding in distributions before the effective date are 
treated as stock or as exercised in appropriate circumstances.
Plan or Arrangement
    Under section 355(d)(7)(B), if two or more persons act pursuant to 
a plan or arrangement with respect to acquisitions of stock or 
securities in Distributing or Controlled, those persons are treated as 
one person for purposes of section 355(d). The proposed regulations 
provide a rule to determine when shareholders act pursuant to a plan or 
arrangement. Under the rule (which does not apply for purposes of any 
other section of the Internal Revenue Code), two or more shareholders 
act pursuant to a plan or arrangement only if they have a formal or 
informal understanding among themselves to make a coordinated 
acquisition of stock. A principal element in determining if such an 
understanding exists is whether the investment decision of each person 
is based on the investment decision of one or more other existing or 
prospective shareholders. Thus, in general, a public offering is not 
treated as a plan or arrangement if each investor makes an independent 
investment decision. This rule applies regardless of the amount of 
stock the shareholders own or acquire. The rule is based on the entity 
rule contained in Sec. 1.382-3(a)(1), and the IRS and Treasury intend 
that the two provisions be administered in a similar manner.
    The proposed regulations provide that creditors' participation in 
an insolvency workout or reorganization in a title 11 or similar case, 
and the receipt of stock in satisfaction of indebtedness in a workout 
or reorganization, are not treated as a plan or arrangement among the 
creditors. The IRS and Treasury request comments as to whether 
additional provisions are appropriate for workout or bankruptcy 
situations, such as rules regarding the timing of purchases of stock 
received by creditors, or rules regarding whether rights created in 
favor of creditors in a bankruptcy case should be treated as options.

(c) Purchase

    Under section 355(d)(5)(A), except as otherwise provided in section 
355(d)(5) (B) and (C), a purchase means any acquisition, but only if 
(1) the basis of the property acquired in the hands of the acquirer is 
not determined in whole or in part by reference to the adjusted basis 
of such property in the hands of the person from whom acquired, or 
under section 1014(a), and (2) the property is not acquired in an 
exchange to which section 351, 354, 355, or 356 applies. The proposed 
regulations clarify that the term exchange in the statute includes a 
reference to all section 355 distributions (for example, spin-offs, 
even though no property is conveyed in exchange for the distributed 
stock).
Exceptions to Definition of Purchase Under Section 355(d)(5)(A)
    The proposed regulations provide that an acquisition of stock 
permitted to be received by a transferor of property without the 
recognition of gain under section 351(a), or permitted to be received 
without the recognition of gain under section 354 or 355, is not a 
purchase to the extent section 358(a)(1) applies to determine the 
recipient's basis, whether or not the recipient also recognizes gain 
under section 351(b) or 356. The Conference Report suggests, at page 
1092, that regulations generally should treat stock received by a 
target corporation shareholder in a reorganization as acquired by 
purchase if the shareholder also receives boot. The Conference Report 
states that purchase treatment is warranted because the basis in the 
shareholder's acquiring corporation stock is increased by the gain the 
shareholder recognizes. However, under section 358(a)(1)(A), the basis 
in the stock also is reduced by the amount of the boot received. Thus, 
the shareholder will not receive a net basis increase in the acquiring 
corporation stock. The proposed regulations also provide that, to the 
extent stock that is ``other property'' under section 351(b) or 
356(a)(1) is

[[Page 23557]]

received in addition to stock excepted from purchase treatment under 
the basic rule, the boot stock is treated as purchased on the date of 
the exchange or distribution for purposes of section 355(d).
    The proposed regulations provide that an acquisition of stock by a 
corporation is generally not a purchase to the extent section 334(b) or 
362 (a) or (b) applies to determine the corporation's basis in the 
stock received. However, because of the basis results, stock is treated 
as purchased on the date of the stock acquisition for purposes of 
section 355(d) if the liquidating corporation recognizes gain or loss 
with respect to the transferred stock as described in section 
334(b)(1), or to the extent the basis of the transferred stock is 
increased through the recognition of gain by the transferor under 
section 362 (a) or (b).
    The proposed regulations provide that, subject to certain 
restrictions, section 305(a) and section 1036(a) transactions are not 
purchases.
Certain Section 351 Exchanges Treated as Purchases
    Under section 355(d)(5)(B), a purchase includes any acquisition of 
property in an exchange to which section 351 applies to the extent the 
property is acquired in exchange for any cash or cash item, any 
marketable stock or security, or any debt of the transferor. The 
property treated as acquired by purchase is the property received by 
the transferor in the exchange. If the transferor receives more than 
one class of stock or securities, or receives both stock and 
securities, the proposed regulations provide that the amount of stock 
or securities purchased is determined in a manner that corresponds to 
the basis allocation under section 358. The proposed regulations define 
the terms cash item and marketable stock to include personal property 
within the meaning of section 1092(d)(1) and Sec. 1.1092(d)-1, without 
giving effect to section 1092(d)(3).
    The proposed regulations provide certain exceptions to purchase 
treatment under section 355(d)(5)(B). Under the first exception, an 
acquisition of stock in a corporation in a section 351(a) transaction 
by one or more persons in exchange for an amount of stock in another 
corporation (the transferred corporation) that meets the requirements 
of section 1504(a)(2) is not a purchase by the transferor or 
transferors, regardless of whether the stock of the transferred 
corporation is marketable stock. Under the second exception, an 
acquisition of stock in exchange for any cash or cash item, any 
marketable stock, or any debt of the transferor in a section 351 
transaction generally is not a purchase if the transferor transfers the 
items as part of an active trade or business and the transferred items 
do not exceed the reasonable needs of the trade or business. This 
exception is based on the Conference Report, at page 1093. The proposed 
regulations provide guidance based on Sec. 1.355-3(b) (2) and (3) for 
determining active conduct of a trade or business and guidance on the 
reasonable needs of the trade or business. All facts and circumstances 
are considered in applying the exception.
    The third exception, also based on the Conference Report, at pages 
1092-93, provides that an acquisition of stock in exchange for any cash 
or cash item, marketable stock or security, or debt of the transferor 
in a section 351 transaction is generally not a purchase if the 
transferor corporation or corporations, the transferee corporation, and 
any distributed controlled corporation of the transferee corporation 
are members of the same affiliated group as defined in section 1504(a) 
before the section 351 transaction (if the transferee corporation is in 
existence before the transaction) and do not cease to be members of 
such affiliated group in any transaction related to the section 351 
transaction (including any distribution of a controlled corporation by 
the transferee corporation). An example illustrates that, under the 
anti-avoidance rule of proposed Sec. 1.355-6(b)(4), this exception does 
not apply if the section 351 transaction is engaged in or structured 
with a principal purpose to avoid the purposes of section 355(d).
    The proposed regulations provide purchase rules for certain 
triangular asset reorganizations. For purposes of section 355(d), the 
proposed regulations generally treat the controlling corporation as 
having acquired the assets and liabilities of the target corporation in 
a transaction in which basis in the acquired assets is determined under 
section 362(b) and then transferred the assets and liabilities to its 
subsidiary corporation in a section 351 transaction. This treatment is 
consistent with the determination of basis in the stock of the 
acquiring subsidiary or target corporation under Sec. 1.358-6. The 
application of section 351 to the deemed asset contribution causes 
section 355(d)(5)(B) (and proposed Sec. 1.355-6(d)(3) (i) through (iv)) 
to apply.
    The proposed regulations provide special rules for transactions 
qualifying as a reorganization under section 368(a)(1)(A) by reason of 
section 368(a)(2)(E) and also as either a reorganization under section 
368(a)(1)(B) or a section 351 transfer. Special rules are necessary for 
these transactions because, under Sec. 1.358-6(c)(2)(ii) or 1.1502-
30(b), a controlling corporation may determine its basis in surviving 
corporation stock by choosing from two alternative methods, but the 
taxpayer need not choose a method until a basis determination is 
relevant. The proposed regulations describe corresponding methods for 
determining the amount of surviving corporation stock treated as 
purchased for purposes of section 355(d). The proposed regulations 
provide that, regardless of which method the controlling corporation 
may actually employ to determine its basis in the surviving corporation 
stock under Sec. 1.358-6(c)(2)(ii) or 1.1502-30(b), the total amount of 
surviving corporation stock treated as purchased immediately after the 
distribution equals the higher of the amount of surviving corporation 
stock that would be treated as purchased under the two alternative 
methods described in proposed Sec. 1.355-6(d)(5)(i). The proposed 
regulations allow a controlling corporation to select one of the two 
alternative methods if the controlling corporation obtains a letter 
ruling and enters into a closing agreement under section 7121 in which 
it agrees to determine its basis in surviving corporation stock using 
the corresponding method under Sec. 1.358-6(c)(2)(ii) (A) or (B). This 
option allows the taxpayer to conform the section 355(d) results with 
the section 358 basis results it chooses.
    Finally, the proposed regulations explain the treatment of group 
structure changes to which Sec. 1.1502-31 applies, and provide rules 
adjusting purchase treatment to conform to basis treatment in 
triangular reorganizations and group structure changes.

(d) Deemed Purchase and Timing Rules

Attribution and Aggregation
    Under section 355(d)(8)(B), if any person purchases an interest in 
an entity, and any stock held by the entity is attributed to the person 
under section 355(d)(8)(A), the person is treated as purchasing the 
stock on the later of the date the person purchased the interest in the 
entity or the date the entity purchased the stock.
    The proposed regulations adopt three additional timing rules based 
on the Conference Report, at page 1090. First, if a person and an 
entity are treated as a single person under section 355(d)(7), and the 
person later purchases an

[[Page 23558]]

additional interest in the entity, the person is treated as purchasing, 
at the time the additional interest is purchased, the amount of stock 
attributed from the entity to the person as a result of the additional 
interest. This timing rule applies even though the person was (prior to 
purchasing the additional interest in the entity) already treated as 
owning all of the stock owned by the entity under the aggregation rules 
of section 355(d)(7). Second, if two persons are treated as one person 
under section 355(d)(7) and one later purchases stock from the other, 
the date of the later purchase is used. Third, if a person who is 
already treated as holding stock under section 355(d)(8)(A) later 
directly purchases such stock, the date of the later direct purchase is 
used. The proposed regulations contain a series of examples, similar to 
those on pages 1090 and 1091 of the Conference Report, demonstrating 
the operation of these rules.
Transferred Basis Rule
    Under section 355(d)(5)(C), if any person acquires property from 
another person who acquired the property by purchase, and the adjusted 
basis of the property in the hands of the acquirer is determined in 
whole or in part by reference to the adjusted basis of the property in 
the hands of the other person, the acquirer is treated as having 
acquired the property by purchase on the date it was acquired by the 
other person. This rule applies, for example, where stock of a 
corporation with a purchased basis is acquired in a section 351 
transfer or a reorganization qualifying under section 368(a)(1)(B), but 
does not apply if the stock of a former common parent is acquired in a 
group structure change.
    Under proposed Sec. 1.355-6(d)(2)(i)(B)(2), transferred stock is 
treated as purchased on the date of a transfer if the stock is 
transferred in a liquidation, and the liquidating corporation 
recognizes gain or loss with respect to the transferred stock as 
described in section 334(b)(1), or to the extent the basis of the 
transferred stock is increased through the recognition of gain by the 
transferor under section 362(a) or (b).
Exchanged Basis Rule
    Based on the Conference Report, at page 1092, the proposed 
regulations adopt a rule that, if any person acquires an interest in an 
entity (the first interest) by purchase, and the first interest is 
exchanged for an interest in another entity (the second interest) where 
the adjusted basis of the second interest is determined by reference to 
the adjusted basis of the first interest, then the second interest is 
treated as having been purchased on the date the first interest was 
purchased. This rule applies, for example, where stock of a corporation 
acquired by purchase is subsequently exchanged for other stock in a 
section 351, 354, or 1036(a) exchange. Under proposed Sec. 1.355-
6(d)(2)(i)(A)(2), stock that is other property under section 351(b) or 
356(a)(1) is treated as purchased on the date of the exchange or 
distribution.
Substantial Diminution of Risk
    As in section 355(d)(6), the proposed regulations provide that the 
running of the five-year period under section 355(d)(3) is suspended 
for any period during which the holder's risk of loss is substantially 
diminished by an option, a short sale, any special class of stock 
(including tracking stock), or any other device or transaction.

(e) Duty to Determine Stockholders and Presumptions

    The proposed regulations provide that, in determining whether 
section 355(d) applies to a distribution, Distributing must determine 
whether a disqualified person holds its stock or the stock of any 
distributed Controlled. For this purpose, a corporation is deemed to 
have knowledge of the existence and contents of all schedules, forms, 
and other documents filed with or under the rules of the Securities and 
Exchange Commission, including, without limitation, any Schedule 13D or 
13G (or any similar schedules) and amendments, with respect to any 
relevant corporation.
    The proposed regulations provide that, absent actual knowledge to 
the contrary, with respect to reporting stock, Distributing may presume 
that all schedules, forms, or other documents are timely filed, 
accurate, and complete. Reporting stock is defined as stock that is 
described in Rule 13d-1(i) of Regulation 13D promulgated under the 
Securities and Exchange Act of 1934. In addition, the proposed 
regulations provide a presumption with respect to less-than-five-
percent shareholders, which are defined as persons that, at no time 
during the five-year period, hold directly (or under the option rules 
contained in the proposed regulations) stock possessing five percent or 
more of the total combined voting power of all classes of stock 
entitled to vote and the total value of shares of all classes of stock 
of a corporation. Absent actual knowledge (or deemed knowledge 
regarding reporting stock) immediately after a distribution to the 
contrary regarding a particular shareholder, Distributing may generally 
presume that no less-than-five-percent shareholder of a corporation 
acquired stock by purchase during the five-year period. This 
presumption does not apply to any less-than-five-percent shareholder 
that, at any time during the five-year period, is related to, acted 
pursuant to a plan or arrangement with, or holds stock that is 
attributed to a shareholder that is not a less-than-five-percent 
shareholder at any time during the five-year period. If an acquiring 
corporation acquires Distributing in a transferred basis transaction, 
Distributing may apply both the reporting stock presumption and the 
less-than-five-percent shareholder presumption to determine whether 
section 355(d) applies to a distribution of Controlled stock to the 
acquiring corporation due to preacquisition stock purchases by 
Distributing's former shareholders.

Proposed Effective Date

    The proposed regulations would apply to distributions occurring 
after the regulations are published as final regulations in the Federal 
Register, except that they would not apply to any distributions 
occurring pursuant to a written agreement which is (subject to 
customary conditions) binding on the date the regulations are published 
as final regulations in the Federal Register, and at all times 
thereafter.

Special Analyses

    It has been determined that this notice of proposed rulemaking is 
not a significant regulatory action as defined in Executive Order 
12866. Therefore, a regulatory assessment is not required. It also has 
been determined that section 553(b) of the Administrative Procedure Act 
(5 U.S.C. chapter 5) does not apply to these regulations, and, because 
the regulations do not impose a collection of information on small 
entities, the Regulatory Flexibility Act (5 U.S.C. chapter 6) does not 
apply. Pursuant to section 7805(f) of the Internal Revenue Code, this 
notice of proposed rulemaking will be submitted to the Chief Counsel 
for Advocacy of the Small Business Administration for comment on its 
impact on small business.

Comments and Public Hearing

    Before these proposed regulations are adopted as final regulations, 
consideration will be given to any written or electronic comments 
(preferably a signed original and eight (8) copies, if written) that 
are submitted timely to the IRS. The IRS and Treasury specifically 
request comments on the clarity of the proposed rule and how it may be 
made easier to understand. All

[[Page 23559]]

comments will be available for public inspection and copying.
    A public hearing has been scheduled for September 21, 1999, 
beginning at 10 a.m. in room 2615 of the Internal Revenue Building, 
1111 Constitution Avenue, NW., Washington, DC. Due to building security 
procedures, visitors must enter at the 10th Street entrance, located 
between Constitution and Pennsylvania Avenues, N.W. In addition, all 
visitors must present photo identification to enter the building. 
Because of access restrictions, visitors will not be admitted beyond 
the immediate entrance area more than 15 minutes before the hearing 
starts. For information about having your name placed on the building 
access list to attend the hearing, see the FOR FURTHER INFORMATION 
CONTACT section of this preamble.
    The rules of 26 CFR 601.601(a)(3) apply to the hearing. Persons who 
wish to present oral comments at the hearing must submit written or 
electronic comments and an outline of the topics to be discussed and 
the time to be devoted to each topic (preferably a signed original and 
eight (8) copies, if written) by August 31, 1999. A period of 10 
minutes will be allotted to each person for making comments. An agenda 
showing the scheduling of the speakers will be prepared after the 
deadline for receiving outlines has passed. Copies of the agenda will 
be available free of charge at the hearing.
    Drafting information. The principal author of these proposed 
regulations is Phoebe Bennett, Office of the Assistant Chief Counsel 
(Corporate). However, other personnel from the IRS and Treasury 
Department participated in their development.

List of Subjects in 26 CFR Part 1

    Income taxes, Reporting and recordkeeping requirements.

Proposed Amendments to the Regulations

    Accordingly, 26 CFR part 1 is proposed to be amended as follows:

PART 1--INCOME TAXES

    Paragraph 1. The authority citation for part 1 is amended by adding 
an entry in numerical order to read in part as follows:

    Authority: 26 U.S.C. 7805 * * *

    Section 1.355-6 also issued under 26 U.S.C. 355(d)(9). * * *

    Par. 2. Section 1.355-0 is amended by;
    1. Revising the section heading.
    2. Revising the entries for Sec. 1.355-6.

    The revisions read as follows:


Sec. 1.355-0  To facilitate the use of Secs. 1.355-1 through 1.355-6, 
this section lists the major paragraphs in those sections.

* * * * *

Sec. 1.355-6  Recognition of gain on certain distributions of stock 
or securities in controlled corporation.

    (a) Conventions.
    (1) Distributing securities.
    (2) Marketable securities.
    (3) Examples.
    (4) Five-year period.
    (b) General rules and purposes of section 355(d).
    (1) Disqualified distributions in general.
    (2) Disqualified stock.
    (i) In general.
    (ii) Purchase.
    (3) Certain distributions not disqualified distributions because 
purposes of section 355(d) not violated.
    (i) In general.
    (ii) Disqualified person.
    (iii) Purchased basis.
    (iv) Purchased interest no longer held.
    (v) Examples.
    (4) Anti-avoidance rule.
    (i) In general.
    (ii) Example.
    (c) Whether a person holds a 50 percent or greater interest.
    (1) In general.
    (2) Valuation.
    (3) Effect of options, warrants, convertible obligations, and 
other similar interests.
    (i) Application.
    (ii) General rule.
    (iii) Options deemed newly issued.
    (A) Exchange, adjustment, or alteration of existing option.
    (B) Certain compensatory options.
    (iv) Effect of treating an option as exercised.
    (A) In general.
    (B) Cash settlement options, phantom stock, stock appreciation 
rights, certain notional principal contracts, or similar interests.
    (C) Stock purchase agreement or similar arrangement.
    (v) Instruments treated as options.
    (vi) Instruments generally not treated as options.
    (A) Escrow, pledge, or other security agreements.
    (B) Compensatory options.
    (1) General rule.
    (2) Exception.
    (C) Certain stock conversion features.
    (D) Options exercisable only upon death, disability, mental 
incompetency, or retirement.
    (E) Rights of first refusal.
    (F) Other enumerated instruments.
    (vii) Reasonably certain that the option will be exercised.
    (A) In general.
    (B) Stock purchase agreement or similar arrangement.
    (viii) Examples.
    (4) Plan or arrangement.
    (i) In general.
    (ii) Understanding.
    (iii) Examples.
    (d) Purchase.
    (1) In general.
    (i) Definition of purchase under section 355(d)(5)(A).
    (ii) Section 355 distributions.
    (iii) Examples.
    (2) Exceptions to definition of purchase under section 
355(d)(5)(A).
    (i) Acquisition of stock in a transaction which includes other 
property or money.
    (A) Transferors and shareholders of transferor or distributing 
corporations.
    (1) In general.
    (2) Exception.
    (B) Transferee corporations.
    (1) In general.
    (2) Exception.
    (C) Examples.
    (ii) Acquisition of stock in a distribution to which section 
305(a) applies.
    (iii) Section 1036(a) exchange.
    (3) Certain section 351 exchanges treated as purchases.
    (i) In general.
    (A) Treatment of stock received by transferor.
    (B) Multiple classes of stock.
    (ii) Cash item, marketable stock.
    (iii) Exception for certain acquisitions.
    (A) In general.
    (B) Example.
    (iv) Exception for assets transferred as part of an active trade 
or business.
    (A) In general.
    (B) Active conduct of a trade or business.
    (C) Reasonable needs of the trade or business.
    (D) Consideration of all facts and circumstances.
    (v) Exception for transfer between members of the same 
affiliated group.
    (A) In general.
    (B) Examples.
    (4) Triangular asset reorganizations.
    (i) Definition.
    (ii) Treatment.
    (iii) Example.
    (5) Reverse triangular reorganizations other than triangular 
asset reorganizations.
    (i) In general.
    (ii) Letter ruling and closing agreement.
    (iii) Examples.
    (6) Treatment of group structure changes.
    (i) In general.
    (ii) Adjustments to basis of higher-tier members.
    (iii) Example.
    (7) Special rules for triangular asset reorganizations, other 
reverse triangular reorganizations, and group structure changes.
    (e) Deemed purchase and timing rules.
    (1) Attribution and aggregation.
    (i) In general.
    (ii) Purchase of additional interest.
    (iii) Purchase between persons treated as one person.
    (iv) Purchase by a person already treated as holding stock under 
section 355(d)(8)(A).
    (v) Examples.
    (2) Transferred basis rule.
    (3) Exchanged basis rule.
    (i) In general.
    (ii) Example.
    (4) Substantial diminution of risk.
    (i) In general.
    (ii) Property to which suspension applies.
    (iii) Risk of loss substantially diminished.

[[Page 23560]]

    (iv) Special class of stock.
    (f) Duty to determine stockholders.
    (1) In general.
    (2) Deemed knowledge of contents of securities filings.
    (3) Presumptions as to securities filings.
    (4) Presumption as to less-than-five-percent shareholders.
    (5) Examples.
    (g) Effective date.

    Par. 3. Section 1.355-6 is revised to read as follows:


Sec. 1.355-6  Recognition of gain on certain distributions of stock or 
securities in controlled corporation.

    (a) Conventions--(1) Distributing securities. Unless otherwise 
stated, any reference in this section to stock of a corporation that is 
(or becomes) a distributing corporation includes a reference to 
securities of the corporation. See section 355(d)(3)(B)(ii)(II) 
(disqualified controlled corporation stock includes controlled 
corporation stock distributed with respect to purchased distributing 
corporation securities).
    (2) Marketable securities. Unless otherwise stated, any reference 
in this section to marketable stock includes a reference to marketable 
securities.
    (3) Examples. For purposes of the examples in this section, unless 
otherwise stated, assume that P, S, T, X, Y, N, HC, D, D1, D2, D3, and 
C are corporations, A and B are individuals, shareholders are not 
treated as one person under section 355(d)(7), stock has been owned for 
more than five years and section 355(d)(6) and paragraph (e)(4) of this 
section do not apply, no election under section 338 (if available) is 
made, and all transactions described are respected under general tax 
principles, including the step transaction doctrine. No inference 
should be drawn from any example as to whether any requirements of 
section 355 other than those of section 355(d), as specified, are 
satisfied.
    (4) Five-year period. For purposes of this section, the term five-
year period means the five-year period (determined after applying 
section 355(d)(6) and paragraph (e)(4) of this section) ending on the 
date of the distribution, but in no event beginning earlier than 
October 10, 1990.
    (b) General rules and purposes of section 355(d)--(1) Disqualified 
distributions in general. In the case of a disqualified distribution, 
any stock or securities in the controlled corporation shall not be 
treated as qualified property for purposes of section 355(c)(2) or 
361(c)(2). In general, a disqualified distribution is any distribution 
to which section 355(or so much of section 356 as relates thereto) 
applies if, immediately after the distribution--
    (i) Any person holds disqualified stock in the distributing 
corporation that constitutes a 50 percent or greater interest in such 
corporation; or
    (ii) Any person holds disqualified stock in the controlled 
corporation (or, if stock of more than one controlled corporation is 
distributed, in any controlled corporation) that constitutes a 50 
percent or greater interest in such corporation.
    (2) Disqualified stock--(i) In general. Disqualified stock is--
    (A) Any stock in the distributing corporation acquired by purchase 
during the five-year period; and
    (B) Any stock in any controlled corporation--
    (1) Acquired by purchase during the five-year period; or
    (2) Received in the distribution to the extent attributable to 
distributions on any stock in the distributing corporation acquired by 
purchase during the five-year period.
    (ii) Purchase. For the definition of a purchase for purposes of 
section 355(d) and this section, see section 355(d)(5) and paragraph 
(d) of this section.
    (3) Certain distributions not disqualified distributions because 
purposes of section 355(d) not violated--(i) In general. 
Notwithstanding the provisions of section 355(d)(2) and this paragraph 
(b), a distribution is not a disqualified distribution if the 
distribution and any related transactions do not violate the purposes 
of section 355(d) as provided in this paragraph (b)(3). A distribution 
does not violate the purposes of section 355(d) if the effect of the 
distribution and any related transactions is neither--
    (A) To increase direct or indirect ownership in the distributing 
corporation or any controlled corporation by a disqualified person; nor
    (B) To provide a disqualified person with a purchased basis in the 
stock of any controlled corporation.
    (ii) Disqualified person. A disqualified person is any person 
(taking into account section 355(d)(7) and paragraph (c)(4) of this 
section) that, immediately after a distribution, holds (directly or 
indirectly under section 355(d)(8) and paragraph (e)(1) of this 
section) disqualified stock in the distributing corporation or 
controlled corporation that constitutes a 50 percent or greater 
interest in such corporation (under section 355(d)(4) and paragraph (c) 
of this section).
    (iii) Purchased basis. A purchased basis is basis in controlled 
corporation stock that is disqualified stock, unless the controlled 
corporation stock and any distributing corporation stock with respect 
to which the controlled corporation stock is distributed are treated as 
acquired by purchase solely under the attribution rules of section 
355(d)(8) and paragraph (e)(1) of this section.
    (iv) Purchased interest no longer held. A person that acquires an 
interest in any entity by purchase ceases to be treated as having 
acquired by purchase stock owned by the entity under section 
355(d)(8)(B) and paragraph (e)(1) of this section at the time when the 
person no longer holds the directly purchased interest.
    (v) Examples. The following examples illustrate this paragraph 
(b)(3):

    Example 1. Stock distributed in spin-off; no purchased basis. D 
owns all of the stock of D1, and D1 owns all the stock of C. A 
purchases 60 percent of the D stock for cash. Within five years of 
A's purchase, D1 distributes the C stock to D. A is treated as 
having purchased 60 percent of the stock of both D1 and C on the 
date A purchases 60 percent of the D stock under the attribution 
rules of section 355(d)(8) and paragraph (e)(1) of this section. The 
C stock received by D is attributable to a distribution on purchased 
D1 stock under section 355(d)(3)(B)(ii). Accordingly, the D1 and C 
stock each is disqualified stock under section 355(d)(3) and 
paragraph (b)(2) of this section, and A is a disqualified person 
under paragraph (b)(3)(ii) of this section. However, the purposes of 
section 355(d) under paragraph (b)(3)(i) of this section are not 
violated. A did not increase direct or indirect ownership in D1 or 
C. In addition, D's basis in the C stock is not a purchased basis 
under paragraph (b)(3)(iii) of this section because both the D1 and 
the C stock are treated as acquired by purchase solely under the 
attribution rules of section 355(d)(8) and paragraph (e)(1) of this 
section. Accordingly, D1's distribution of the C stock to D is not a 
disqualified distribution under section 355(d)(2) and paragraph 
(b)(1) of this section.
    Example 2. Stock distributed in spin-off; purchased basis. The 
facts are the same as Example 1, except that D immediately further 
distributes the C stock to its shareholders (including A) pro rata. 
The D and C stock each is disqualified stock under section 355(d)(3) 
and paragraph (b)(2) of this section, and A is a disqualified person 
under paragraph (b)(3)(ii) of this section. The purposes of section 
355(d) under paragraph (b)(3)(i) of this section are violated. A did 
not increase direct or indirect ownership in D or C. However, A's 
basis in the C stock is a purchased basis under paragraph 
(b)(3)(iii) of this section because the D stock is not treated as 
acquired by purchase solely under the attribution rules of section 
355(d)(8) and paragraph (e)(1) of this section. Accordingly, the 
further distribution is a disqualified distribution under section 
355(d)(2) and paragraph (b)(1) of this section.
    Example 3. Stock distributed in split-off with ownership 
increase; purchased basis. The facts are the same as Example 1, 
except

[[Page 23561]]

that D immediately further distributes the C stock to A in exchange 
for A's purchased stock in D. The C stock received by A is 
attributable to a distribution on purchased D stock under section 
355(d)(3)(B)(ii), and A's basis in the C stock is determined by 
reference to the adjusted basis of A's purchased D stock under 
paragraph (e)(3) of this section. Accordingly, the D stock and the C 
stock each is disqualified stock under section 355(d)(3) and 
paragraph (b)(2) of this section, and A is a disqualified person 
under paragraph (b)(3)(ii) of this section. The purposes of section 
355(d) under paragraph (b)(3)(i) of this section are violated 
because A increased its ownership in C from a 60 percent indirect 
interest to a 100 percent direct interest, and because A's basis in 
the C stock is a purchased basis under paragraph (b)(3)(iii) of this 
section. Accordingly, the further distribution is a disqualified 
distribution under section 355(d)(2) and paragraph (b)(1) of this 
section.
    Example 4. Stock distributed in spin-off; purchased basis. D1 
owns all the stock of C. D purchases all of the stock of D1 for 
cash. Within five years of D's purchase of D1, P acquires all of the 
stock of D1 from D in a section 368(a)(1)(B) reorganization that is 
not a reorganization under section 368(a)(1)(A) by reason of section 
368(a)(2)(E), and D1 distributes all of its C stock to P. P is 
treated as having acquired the D1 stock by purchase on the date D 
acquired it under the transferred basis rule of section 355(d)(5)(C) 
and paragraph (e)(2) of this section. P is treated as having 
purchased all of the C stock on the date D purchased the D1 stock 
under the attribution rules of section 355(d)(8) and paragraph 
(e)(1) of this section, and the C stock received by P is 
attributable to a distribution on purchased D1 stock under section 
355(d)(3)(B)(ii). Accordingly, the D1 and C stock each is 
disqualified stock under section 355(d)(3) and paragraph (b)(2) of 
this section, and P is a disqualified person under paragraph 
(b)(3)(ii) of this section. The purposes of section 355(d) under 
paragraph (b)(3)(i) of this section are violated. P did not increase 
direct or indirect ownership in D1 or C. However, P's basis in the C 
stock is a purchased basis under paragraph (b)(3)(iii) of this 
section because the D1 stock is not treated as acquired by purchase 
solely under the attribution rules of section 355(d)(8) and 
paragraph (e)(1) of this section. Accordingly, D1's distribution of 
the C stock to P is a disqualified distribution under section 
355(d)(2) and paragraph (b)(1) of this section.
    Example 5. Stock distributed in split-off with ownership 
increase; no purchased basis. P owns 50 percent of the stock of D, 
the remaining D stock is owned by unrelated persons, D owns all the 
stock of C, and A purchases all of the P stock from the P 
shareholders. Within five years of A's purchase, D distributes all 
of the C stock to P in exchange for P's D stock. A is treated as 
having purchased 50 percent of the stock of both D and C on the date 
A purchases the P stock under the attribution rules of section 
355(d)(8) and paragraph (e)(1) of this section. The C stock received 
by P is attributable to a distribution on purchased D stock under 
section 355(d)(3)(B)(ii). Accordingly, the D stock and the C stock 
each is disqualified stock under section 355(d)(3) and paragraph 
(b)(2) of this section, and A is a disqualified person under 
paragraph (b)(3)(ii) of this section. The purposes of section 355(d) 
under paragraph (b)(3)(i) of this section are violated because, even 
though P's basis in the C stock is not a purchased basis under 
paragraph (b)(3)(iii) of this section, A increased its direct or 
indirect ownership in C from a 50 percent indirect interest to a 100 
percent indirect interest. Accordingly, D's distribution of the C 
stock to P is a disqualified distribution under section 355(d)(2) 
and paragraph (b)(1) of this section.
    Example 6. Stock distributed in split-off with no ownership 
increase; no purchased basis. A purchases all of the stock of T. T 
later merges into D in a section 368(a)(1)(A) reorganization and A 
exchanges its purchased T stock for 60 percent of the stock of D. D 
owns all of the stock of D1 and D2, D1 and D2 each owns 50 percent 
of the stock of D3, and D3 owns all of the stock of C. Within five 
years of A's purchase of the T stock, D3 distributes the C stock to 
D1 in exchange for all of D1's D3 stock. A is treated as having 
acquired 60 percent of the D stock by purchase on the date A 
purchases the T stock under paragraph (e)(3) of this section. A is 
treated as having purchased 60 percent of the stock of D1, D2, D3, 
and C on the date A purchases the T stock under the attribution 
rules of section 355(d)(8) and paragraph (e)(1) of this section. The 
C stock received by D1 is attributable to a distribution on 
purchased D3 stock under section 355(d)(3)(B)(ii). Accordingly, the 
D3 stock and the C stock each is disqualified stock under section 
355(d)(3) and paragraph (b)(2) of this section, and A is a 
disqualified person under paragraph (b)(3)(ii) of this section. 
However, the purposes of section 355(d) under paragraph (b)(3)(i) of 
this section are not violated. A did not increase direct or indirect 
ownership in D3 or C, and D1's basis in the C stock is not a 
purchased basis under paragraph (b)(3)(iii) of this section because 
the D3 stock is treated as acquired by purchase solely under the 
attribution rules of section 355(d)(8) and paragraph (e)(1) of this 
section. Accordingly, D3's distribution of the C stock to D1 is not 
a disqualified distribution under section 355(d)(2) and paragraph 
(b)(1) of this section.
    Example 7. Purchased basis eliminated by liquidation; stock 
distributed in spin-off. P owns 30 percent of the stock of D, D owns 
all of the stock of D1, and D1 owns all of the stock of C. P 
purchases the remaining 70 percent of the D stock for cash. Within 
five years of P's purchase, P liquidates D in a transaction 
qualifying under sections 332 and 337(a), and D1 then distributes 
the stock of C to P. Prior to the liquidation, P is treated as 
having purchased 70 percent of the stock of D1 and C on the date P 
purchases the D stock under the attribution rules of section 
355(d)(8)(B) and paragraph (e)(1) of this section. After the 
liquidation, however, under paragraph (b)(3)(iv) of this section, P 
is not treated as having acquired by purchase the D1 or the C stock 
under section 355(d)(8)(B) and paragraph (e)(1) of this section 
because P no longer holds the directly purchased interest in D. 
Under section 334(b)(1), P's basis in the D1 stock is determined by 
reference to D's basis in the D1 stock and not by reference to P's 
basis in D. Paragraph (d)(2)(i)(B) of this section does not treat 
the D1 stock as newly purchased in P's hands because no gain or loss 
was recognized by D in the liquidation. Accordingly, neither the D1 
stock nor the C stock is disqualified stock under section 355(d)(3) 
and paragraph (b)(2) of this section in P's hands, and the 
distribution is not a disqualified distribution under section 
355(d)(2) and paragraph (b)(1) of this section.
    Example 8. Purchased basis eliminated by upstream merger; stock 
distributed in spin-off. D owns all of the stock of D1, and D1 owns 
all of the stock of C. P purchases 60 percent of the D stock for 
cash. Within five years of P's purchase, D merges into P in a 
section 368(a)(1)(A) reorganization, with the D shareholders other 
than P receiving solely P stock in exchange for their D stock, and 
D1 then distributes the stock of C to P. Prior to the merger, P is 
treated as having purchased 60 percent of the stock of D1 and C on 
the date P purchases the D stock under the attribution rules of 
section 355(d)(8) and paragraph (e)(1) of this section. After the 
merger, however, under paragraph (b)(3)(iv) of this section, P is 
not treated as having acquired by purchase the D1 or the C stock 
under section 355(d)(8)(B) and paragraph (e)(1) of this section 
because P no longer holds the directly purchased interest in D. 
Under section 362(b), P's basis in the D1 stock is determined by 
reference to D's basis in the D1 stock and not by reference to P's 
basis in D. Paragraph (d)(2)(i)(B) of this section does not treat 
the D1 stock as newly purchased in P's hands because no gain or loss 
was recognized by D in the merger. Accordingly, neither the D1 stock 
nor the C stock is disqualified stock under section 355(d)(3) and 
paragraph (b)(2) of this section in P's hands, and the distribution 
is not a disqualified distribution under section 355(d)(2) and 
paragraph (b)(1) of this section.

    (4) Anti-avoidance rule--(i) In general. Notwithstanding any 
provision of section 355(d) or this section, the Commissioner may treat 
any distribution as a disqualified distribution under section 355(d)(2) 
and paragraph (b)(1) of this section if the distribution or another 
transaction or transactions are engaged in or structured with a 
principal purpose to avoid the purposes of section 355(d) or this 
section with respect to the distribution. Without limiting the 
preceding sentence, the Commissioner may determine that the existence 
of a related person, intermediary, pass-through entity, or similar 
person (an intermediary) should be disregarded, in whole or in part, if 
the intermediary is formed or availed of with a principal purpose to 
avoid the purposes of section 355(d) or this section.
    (ii) Example. The following example illustrates this paragraph 
(b)(4):

    Example. Post-distribution redemption. B wholly owns D, which 
wholly owns C. With a principal purpose to avoid the purposes of

[[Page 23562]]

section 355(d), A, B, D, and C engage in the following transactions. 
A purchases 45 of 100 shares of the only class of D stock. Within 
five years after A's purchase, D distributes all of its 100 shares 
in C to A and B pro rata. D then redeems 20 shares of B's D stock, 
and C redeems 20 shares of B's C stock. After the redemption, A owns 
45 shares and B owns 35 shares in each of D and C. Under paragraph 
(b)(4)(i) of this section, the Commissioner may treat A as owning 
disqualified stock in D and C that constitutes a 50 percent or 
greater interest in D and C immediately after the distribution. 
Under that treatment, the distribution is a disqualified 
distribution under section 355(d)(2).

    (c) Whether a person holds a 50 percent or greater interest--(1) In 
general. Under section 355(d)(4), 50 percent or greater interest means 
stock possessing at least 50 percent of the total combined voting power 
of all classes of stock entitled to vote or at least 50 percent of the 
total value of shares of all classes of stock.
    (2) Valuation. For purposes of section 355(d)(4) and this section, 
all shares of stock within a single class are considered to have the 
same value. But see paragraph (c)(3)(vii)(A) of this section 
(determination of whether it is reasonably certain that an option will 
be exercised).
    (3) Effect of options, warrants, convertible obligations, and other 
similar interests--(i) Application. This paragraph (c)(3) provides 
rules to determine when an option is treated as exercised for purposes 
of section 355(d) (other than section 355(d)(6)). Except as provided in 
this paragraph (c)(3), an option is not treated as exercised for 
purposes of section 355(d). This paragraph (c)(3) does not affect the 
determination of whether an instrument is an option or stock under 
general principles of tax law (such as substance over form).
    (ii) General rule. In determining whether a person has acquired by 
purchase a 50 percent or greater interest under section 355(d)(4), an 
option to acquire stock (as described in paragraphs (c)(3) (v) and (vi) 
of this section) that has not been exercised when a distribution occurs 
is treated as exercised on the date it was issued or most recently 
transferred if--
    (A) Its exercise (whether by itself or in conjunction with the 
deemed exercise of one or more other options) would cause a person to 
become a disqualified person; and
    (B) Immediately after the distribution, it is reasonably certain 
(as described in paragraph (c)(3)(vii) of this section) that the option 
will be exercised.
    (iii) Options deemed newly issued--(A) Exchange, adjustment, or 
alteration of existing option. For purposes of this paragraph (c)(3), 
each of the following is treated as a new issuance or transfer of an 
existing option only if it materially increases the likelihood that an 
option will be exercised--
    (1) An exchange of an option for another option or options;
    (2) An adjustment to the terms of an option (including an 
adjustment pursuant to the terms of the option);
    (3) An adjustment to the terms of the underlying stock (including 
an adjustment pursuant to the terms of the stock);
    (4) A change to the capital structure of the issuing corporation; 
and
    (5) An alteration to the fair market value of issuing corporation 
stock through an asset transfer (other than regular, ordinary 
dividends) or through any other means.
    (B) Certain compensatory options. An option described in paragraph 
(c)(3)(vi)(B)(2) of this section is treated as issued on the date it 
becomes transferable.
    (iv) Effect of treating an option as exercised--(A) In general. For 
purposes of section 355(d), an option that is treated as exercised 
under this paragraph (c)(3) is treated as exercised both for purposes 
of determining the percentage of the voting power of stock owned by the 
holder and for purposes of determining the percentage of the value of 
stock owned by the holder.
    (B) Cash settlement options, phantom stock, stock appreciation 
rights, certain notional principal contracts, or similar interests. If 
a cash settlement option, phantom stock, stock appreciation right, 
notional principal contract described in paragraph (c)(3)(v)(B) of this 
section, or similar interest is treated as exercised, the option is 
treated as having been converted into stock of the issuing corporation. 
If the amount to be received upon the exercise of such an option is 
determined by reference to a multiple of the increase in the value of a 
share of the issuing corporation's stock on the exercise date over the 
value of a share of the stock on the date the option is issued, the 
option is treated as converted into a corresponding number of shares of 
such stock. Appropriate adjustments must be made in any situation in 
which the amount to be received upon exercise of the option is 
determined in another manner.
    (C) Stock purchase agreement or similar arrangement. If a stock 
purchase agreement or similar arrangement is deemed exercised, the 
purchaser is treated as having purchased of the stock under the terms 
of the agreement or arrangement as though all covenants had been 
satisfied and all contingencies met. The agreement or arrangement is 
deemed to have been exercised as of the date it is entered into or most 
recently assigned.
    (v) Instruments treated as options. For purposes of this paragraph 
(c)(3), except to the extent provided in paragraph (c)(3)(vi) of this 
section, the following are treated as options:
    (A) A call option, warrant, convertible obligation, the conversion 
feature of convertible stock, put option, redemption agreement 
(including a right to cause the redemption of stock), notional 
principal contract (as defined in Sec. 1.446-3(c)) that provides for 
the payment of amounts in stock, stock purchase agreement or similar 
arrangement, or any other instrument that provides for the right to 
purchase, issue, redeem, or transfer stock (including an option on an 
option).
    (B) A cash settlement option, phantom stock, stock appreciation 
right, notional principal contract (as defined in Sec. 1.446-3(c)) that 
provides for payment based on the price of stock, or any other similar 
interest (except for stock).
    (vi) Instruments generally not treated as options. For purposes of 
this paragraph (c)(3), the following are not treated as options, unless 
issued, transferred, or listed with a principal purpose to avoid the 
application of section 355(d) or this section:
    (A) Escrow, pledge, or other security agreements. An option that is 
part of a security arrangement in a typical lending transaction 
(including a purchase money loan), if the arrangement is subject to 
customary commercial conditions. For this purpose, a security 
arrangement includes, for example, an agreement for holding stock in 
escrow or under a pledge or other security agreement, or an option to 
acquire stock contingent upon a default under a loan.
    (B) Compensatory options--(1) General rule. An option to acquire 
stock in a corporation with customary terms and conditions provided to 
an employee, director, or independent contractor in connection with the 
performance of services for the corporation or a person related to it 
under section 355(d)(7)(A) (and that is not excessive by reference to 
the services performed) and that--
    (i) Is nontransferable within the meaning of Sec. 1.83-3(d); and
    (ii) Does not have a readily ascertainable fair market value as 
defined in Sec. 1.83-7(b).
    (2) Exception. Paragraph (c)(3)(vi)(B)(1) of this section ceases to 
apply to an option that becomes transferable.

[[Page 23563]]

    (C) Certain stock conversion features. The conversion feature of 
convertible stock, provided that--
    (1) The stock is not convertible for at least five years after 
issuance or transfer; and
    (2) The terms of the conversion feature do not require the tender 
of any consideration other than the stock being converted.
    (D) Options exercisable only upon death, disability, mental 
incompetency, or retirement. Any option entered into between 
stockholders of a corporation (or a stockholder and the corporation) 
with respect to the stock of either stockholder that is exercisable 
only upon the death, disability, mental incompetency of the 
stockholder, or, in the case of stock acquired in connection with the 
performance of services for the corporation or a person related to it 
under section 355(d)(7)(A) (and that is not excessive by reference to 
the services performed), the stockholder's retirement.
    (E) Rights of first refusal. A bona fide right of first refusal 
regarding the corporation's stock with customary terms, entered into 
between stockholders of a corporation (or between the corporation and a 
stockholder).
    (F) Other enumerated instruments. Any other instruments specified 
in regulations, a revenue ruling, or a revenue procedure. See 
Sec. 601.601(d)(2) of this chapter.
    (vii) Reasonably certain that the option will be exercised--(A) In 
general. The determination of whether, immediately after the 
distribution, an option is reasonably certain to be exercised is based 
on all the facts and circumstances. In applying the previous sentence, 
the fair market value of stock underlying an option is determined by 
taking into account control premiums and minority and blockage 
discounts.
    (B) Stock purchase agreement or similar arrangement. A stock 
purchase agreement or similar arrangement is treated as reasonably 
certain to be exercised if the parties' obligations to complete the 
transaction are subject only to reasonable closing conditions.
    (viii) Examples. The following examples illustrate this paragraph 
(c)(3):

    Example 1. D owns all of the stock of C. A purchases 40 percent 
of D's only class of stock and an option to purchase an additional 
20 percent of the D stock. Assume that no control premium or 
minority or blockage discount applies to the D stock underlying the 
option. The option permits A to acquire the stock at $30 per share, 
and D's stock has a fair market value of $27 per share on the date 
the option is issued. The option is subject to no contingencies or 
restrictive covenants, may be exercised within five years after its 
issuance, and is not described in paragraph (c)(3)(vi) of this 
section (regarding instruments generally not treated as options). 
Within five years of A's purchase of the D stock and option, D 
distributes the stock of its subsidiary C pro rata and A receives 40 
percent of the C stock in the distribution. Immediately after the 
distribution, D's stock has a fair market value of $30 per share and 
C's stock has a fair market value of $15 per share. At the time of 
the distribution, A exchanges A's option for an option to purchase 
20 percent of the D stock at $20 per share and an option to purchase 
20 percent of the C stock at $10 per share. Based on all the facts 
and circumstances, it is reasonably certain, immediately after the 
distribution, that A will exercise its options. Under paragraph 
(c)(3)(iii)(A)(1) of this section, the substituted options are 
treated as issued on the date the original option was issued. 
Accordingly, the options are treated as exercised by A on the date 
that A purchased the original option. A is treated as owning 60 
percent of the D stock and 60 percent of the C stock that is 
disqualified stock, and the distribution is a disqualified 
distribution under section 355(d)(2) and paragraph (b)(1) of this 
section.
    Example 2. D owns all of the stock of C. A purchases 37 percent 
of D's only class of stock. B owns 38 percent of the D stock, and 
the remaining 25 percent is owned by 20 individuals, each of whom 
owns less than five percent of D's stock. A purchases an option to 
purchase an additional 14 percent of the D stock from shareholders 
other than B for $50 per share. The option is subject to no 
contingencies or restrictive covenants, may be exercised within five 
years after its issuance, and is not described in paragraph 
(c)(3)(vi) of this section. Within five years of A's purchase of the 
option and 37 percent interest in D, D distributes the stock of its 
subsidiary C pro rata and A receives 37 percent of the C stock in 
the distribution. At the time of the distribution, A exchanges its 
option for an option to purchase 14 percent of the D stock at $25 
per share and an option to purchase 14 percent of the C stock at $25 
per share. Assume that, although a shareholder that owned no D or C 
stock would pay only $20 per share for D or C stock immediately 
after the distribution, a shareholder in A's position would pay $30 
per share for 14 percent of the stock of D or C because of the 
control premium which attaches to the shares. The control premium is 
taken into account under paragraph (c)(3)(vii)(A) of this section to 
determine whether A is reasonably certain to exercise the options. 
Based on all the facts and circumstances, it is reasonably certain, 
immediately after the distribution, that A will exercise its 
options. Under paragraph (c)(3)(iii)(A) of this section, the 
substituted options are treated as issued on the date the original 
option was issued. Accordingly, the options are treated as exercised 
by A on the date that A purchased the original option. Under 
paragraph (c)(2) of this section, all shares of D and C are 
considered to have the same value to determine the amount of stock A 
is treated as purchasing under the options. A is treated as owning 
51 percent of the D stock and 51 percent of the C stock that is 
disqualified stock, and the distribution is a disqualified 
distribution under section 355(d)(2).

    (4) Plan or arrangement--(i) In general. Under section 
355(d)(7)(B), if two or more persons act pursuant to a plan or 
arrangement with respect to acquisitions of stock in the distributing 
corporation or controlled corporation, those persons are treated as one 
person for purposes of section 355(d).
    (ii) Understanding. For purposes of section 355(d)(7)(B), two or 
more persons who are (or will after an acquisition become) shareholders 
(or are treated as shareholders under paragraph (c)(3)(ii) of this 
section) act pursuant to a plan or arrangement with respect to an 
acquisition of stock only if they have a formal or informal 
understanding among themselves to make a coordinated acquisition of 
stock. A principal element in determining if such an understanding 
exists is whether the investment decision of each person is based on 
the investment decision of one or more other existing or prospective 
shareholders. However, the participation by creditors in formulating a 
plan for an insolvency workout or a reorganization in a title 11 or 
similar case (whether as members of a creditors' committee or 
otherwise) and the receipt of stock by creditors in satisfaction of 
indebtedness pursuant to the workout or reorganization do not cause the 
creditors to be considered as acting pursuant to a plan or arrangement.
    (iii) Examples. The following examples illustrate paragraph 
(c)(4)(ii) of this section:

    Example 1. D has 1,000 shares of common stock outstanding. A 
group of 20 unrelated individuals who previously owned no D stock 
(the Group) agree among themselves to acquire 50 percent or more of 
D's stock. The Group is not a person under section 7701(a)(1). 
Subsequently, pursuant to their understanding, the members of the 
Group purchase 600 shares of D common stock from the existing D 
shareholders (a total of 60 percent of the D stock), with each 
member purchasing 30 shares. Under paragraph (c)(4)(ii) of this 
section, the members of the Group have a formal or informal 
understanding among themselves to make a coordinated acquisition of 
stock. Their interests are therefore aggregated under section 
355(d)(7)(B), and they are treated as one person who purchased 600 
shares of D's stock for purposes of section 355(d).
    Example 2. D has 1,000 shares of outstanding stock owned by 
unrelated individuals. D's management is concerned that D may become 
subject to a takeover bid. In separate meetings, D's management 
meets with potential investors who own no stock and are friendly to 
management to convince them to acquire D's stock based on an 
understanding that D will assemble a group

[[Page 23564]]

that in the aggregate will acquire more than 50 percent of D's 
stock. Subsequently, 15 of these investors each purchases four 
percent of D's stock. Under paragraph (c)(4)(ii) of this section, 
the 15 investors have a formal or informal understanding among 
themselves to make a coordinated acquisition of stock. Their 
interests are therefore aggregated under section 355(d)(7)(B), and 
they are treated as one person who purchased 600 shares of D stock 
for purposes of section 355(d).
    Example 3. (i) D has 1,000 shares of outstanding stock owned by 
unrelated individuals. An investment advisor advises its clients 
that it believes D's stock is undervalued and recommends that they 
acquire D stock. Acting on the investment advisor's recommendation, 
20 unrelated individuals each purchases 30 shares of D stock. Each 
client's decision was not based on the investment decisions made by 
one or more other clients. Because there is no formal or informal 
understanding among the clients to make a coordinated acquisition of 
D stock, their interests are not aggregated under section 
355(d)(7)(B) and they are treated as making separate purchases.
    (ii) The facts are the same as in paragraph (i) of this Example 
3, except that the investment advisor is also the underwriter 
(without regard to whether it is a firm commitment or best efforts 
underwriting) for a primary or secondary offering of D stock. The 
result is the same.
    (iii) The facts are the same as in paragraph (i) of this Example 
3, except that, instead of an investment advisor recommending that 
clients purchase D stock, the trustee of several trusts qualified 
under section 401(a) sponsored by unrelated corporations causes each 
trust to purchase the D stock. The result is the same, provided that 
the trustee's investment decision made on behalf of each trust was 
not based on the investment decision made on behalf of one or more 
of the other trusts.
    (d) Purchase--(1) In general--(i) Definition of purchase under 
section 355(d)(5)(A). Under section 355(d)(5)(A), except as otherwise 
provided in section 355(d)(5)(B) and (C), a purchase means any 
acquisition, but only if--
    (A) The basis of the property acquired in the hands of the acquirer 
is not determined--
    (1) In whole or in part by reference to the adjusted basis of such 
property in the hands of the person from whom acquired; or
    (2) Under section 1014(a); and
    (B) The property is not acquired in an exchange to which section 
351, 354, 355, or 356 applies.
    (ii) Section 355 distributions. Paragraph (d)(1)(i)(B) of this 
section includes all section 355 distributions, whether in exchange (in 
whole or in part) for stock or pro rata.

    (iii) Examples. The following examples illustrate this paragraph 
(d)(1):

    Example 1. Section 304(a)(1) acquisition. A, who owns all of the 
stock of P and T, sells the T stock to P for cash. The T stock is 
not marketable stock under section 355(d)(5)(B)(ii) and paragraph 
(d)(3)(ii) of this section. A is treated under section 304(a)(1) as 
receiving a distribution in redemption of the P stock. Under section 
302(d), the deemed redemption is treated as a section 301 
distribution. Assume that under sections 304(b)(2) and 301(c)(1), 
all of the distribution is a dividend. A and P are treated in the 
same manner as if A had transferred the T stock to P in exchange for 
stock of P in a transaction to which section 351(a) applies, and P 
had then redeemed the stock P was treated as issuing in the 
transaction. Under section 362(a), P's basis in the T stock is 
determined by reference to A's adjusted basis in the T stock, and 
there is no basis increase in the T stock because A recognizes no 
gain on the deemed transfer. Accordingly, P's acquisition of the T 
stock from A is not a purchase by P under section 355(d)(5)(A)(i)(I) 
and paragraphs (d)(1)(i)(A)(1) and (d)(2)(i)(B) of this section.
    Example 2. Section 338 election. P owns all of the stock of S 
and no other assets. X acquires all of the P stock from the P 
shareholders and makes an election under section 338. Under section 
355(d)(5)(A), X has acquired the P stock by purchase. Under section 
338(a) and (b), P is treated as having sold all of its assets at 
fair market value and purchased the assets as a new corporation as 
of the beginning of the day after the acquisition date for an amount 
equal to the purchase price of the P stock. Accordingly, P is 
treated as having purchased all of the S stock under section 
355(d)(5)(A).

    (2) Exceptions to definition of purchase under section 
355(d)(5)(A). The following acquisitions are not treated as purchases 
under section 355(d)(5)(A):
    (i) Acquisition of stock in a transaction which includes other 
property or money--(A) Transferors and shareholders of transferor or 
distributing corporations--(1) In general. An acquisition of stock 
permitted to be received by a transferor of property without the 
recognition of gain under section 351(a), or permitted to be received 
without the recognition of gain under section 354 or 355, is not a 
purchase to the extent section 358(a)(1) applies to determine the 
recipient's basis in the stock received, whether or not the recipient 
also recognizes gain under section 351(b) or 356. But see paragraph 
(e)(3) of this section (interest received in exchange for purchased 
interest in exchanged basis transaction treated as purchased).
    (2) Exception. To the extent there is received in the exchange or 
distribution, in addition to stock described in paragraph 
(d)(2)(i)(A)(1) of this section, stock that is other property under 
section 351(b) or 356(a)(1), the stock is treated as purchased on the 
date of the exchange or distribution for purposes of section 355(d).
    (B) Transferee corporations--(1) In general. An acquisition of 
stock by a corporation is not a purchase to the extent section 334(b) 
or 362(a) or (b) applies to determine the corporation's basis in the 
stock received. But see section 355(d)(5)(C) and paragraph (e)(2) of 
this section (purchased property transferred in transferred basis 
transaction is treated as purchased by transferee).
    (2) Exception. If a corporation acquires stock, the stock is 
treated as purchased on the date of the stock acquisition for purposes 
of section 355(d)--
    (i) If the liquidating corporation recognizes gain or loss with 
respect to the transferred stock as described in section 334(b)(1); or
    (ii) To the extent the basis of the transferred stock is increased 
through the recognition of gain by the transferor under section 362(a) 
or (b).
    (C) Examples. The following examples illustrate this paragraph 
(d)(2)(i):

    Example 1. (i) A owns all the stock of T. T merges into D in a 
transaction qualifying under section 368(a)(1)(A), with A exchanging 
all of the T stock for D stock and $100 cash. Under section 
356(a)(1), A recognizes $100 of the realized gain on the 
transaction. Under section 358(a)(1), A's basis in the D stock 
equals A's basis in the T stock, decreased by the $100 received and 
increased by the gain recognized, also $100. Under paragraph 
(d)(2)(i)(A) of this section, A is not treated as having purchased 
the D stock for purposes of section 355(d)(5).
    (ii) The facts are the same as in paragraph (i) of this Example, 
except that rather than D stock and $100 cash, A receives D stock 
and stock in C, a corporation not a party to the reorganization, 
with a fair market value of $100. Under section 358(a)(2), A's basis 
in the C stock is its fair market value, or $100. Under paragraph 
(d)(2)(i)(A)(2) of this section, A is treated as having purchased 
the C stock, but not the D stock, for purposes of section 355(d)(5).
    Example 2. A purchases all of the stock of D, which is not 
marketable stock, on Date 1 for $90. Within five years of A's 
purchase, on Date 2, A contributes the D stock to P in exchange for 
P stock worth $90 and $10 cash in a transaction qualifying under 
section 351. Under section 362(a), P's basis in D is $100. P is 
treated as having purchased 90 percent ($90 worth) of the D stock on 
Date 1 under section 355(d)(5)(C) and paragraph (e)(2)(i) of this 
section and as having purchased 10 percent ($10 worth) of the D 
stock on Date 2 under paragraph (d)(2)(i)(B)(2) of this section.

    (ii) Acquisition of stock in a distribution to which section 305(a) 
applies. An acquisition of stock in a distribution qualifying under 
section 305(a) is not a purchase to the extent section 307(a) applies 
to determine the recipient's basis. However, to the extent

[[Page 23565]]

the distribution is of rights to acquire stock, see paragraph (c)(3) of 
this section for rules regarding options, warrants, convertible 
obligations, and other similar interests.
    (iii) Section 1036(a) exchange. An exchange of stock qualifying 
under section 1036(a) is not a purchase by either party to the exchange 
to the extent the basis of the property acquired equals that of the 
property exchanged under section 1031(d).
    (3) Certain section 351 exchanges treated as purchases--(i) In 
general--(A) Treatment of stock received by transferor. Under section 
355(d)(5)(B), a purchase includes any acquisition of property in an 
exchange to which section 351 applies to the extent the property is 
acquired in exchange for any cash or cash item, any marketable stock, 
or any debt of the transferor. The property treated as acquired by 
purchase is the property received by the transferor in the exchange.
    (B) Multiple classes of stock. If the transferor in a transaction 
described in section 355(d)(5)(B) receives stock or securities of more 
than one class, or receives both stock and securities, then the amount 
of stock or securities purchased is determined in a manner that 
corresponds to the allocation of basis to the stock or securities under 
section 358. See Sec. 1.358-2(b).
    (ii) Cash item, marketable stock. For purposes of section 
355(d)(5)(B) and this paragraph (d)(3), either or both of the terms 
cash item and marketable stock include personal property within the 
meaning of section 1092(d)(1) and Sec. 1.1092(d)-1, without giving 
effect to section 1092(d)(3).
    (iii) Exception for certain acquisitions--(A) In general. Except to 
the extent provided in paragraph (e)(3) of this section (interest 
received in exchange for purchased interest in exchanged basis 
transaction treated as purchased), an acquisition of stock in a 
corporation in a section 351 transaction by one or more persons in 
exchange for an amount of stock in another corporation (the transferred 
corporation) that meets the requirements of section 1504(a)(2) is not a 
purchase by the transferor or transferors, regardless of whether the 
stock of the transferred corporation is marketable stock under section 
355(d)(5)(B)(ii) and paragraph (d)(3)(ii) of this section.
    (B) Example. The following example illustrates this paragraph 
(d)(3)(iii):

    Example. D's two classes of stock, voting common and nonvoting 
preferred, are both widely held and publicly traded. The nonvoting 
preferred stock is stock described in section 1504(a)(4). Assume 
that all of the D stock is marketable stock under section 
355(d)(5)(B)(ii) and paragraph (d)(3)(ii) of this section. D's board 
of directors proposes that, for valid business purposes, D's common 
stock should be held by a holding company, HC, but its preferred 
stock should not be transferred to HC. As proposed, the D common 
shareholders exchange their D stock solely for HC common stock in a 
section 351(a) transaction. The D preferred shareholders retain 
their stock. HC acquires an amount of D stock that meets the 
requirements of section 1504(a)(2). Although the D common stock was 
marketable stock in the hands of the D shareholders immediately 
before the transfer, and the D nonvoting preferred stock is 
marketable stock after the transfer, the D shareholders are not 
treated as having acquired the HC stock by purchase (except to the 
extent the exchanged basis rule of paragraph (e)(3) of this section 
may apply to treat HC stock as purchased on the date the exchanged D 
stock was purchased).

    (iv) Exception for assets transferred as part of an active trade or 
business--(A) In general. Except to the extent provided in paragraph 
(e)(3) of this section, an acquisition not described in paragraph 
(d)(3)(iii) of this section of stock in exchange for any cash or cash 
item, any marketable stock, or any debt of the transferor in a section 
351 transaction is not a purchase if--
    (1) The transferor is engaged in the active conduct of a trade or 
business under paragraph (d)(3)(iv)(B) of this section and the 
transferred items (including debt incurred in the ordinary course of 
the trade or business) are used in the trade or business;
    (2) The transferred items do not exceed the reasonable needs of the 
trade or business under paragraph (d)(3)(iv)(C) of this section;
    (3) The transferor transfers the items as part of the trade or 
business; and
    (4) The transferee continues the active conduct of the trade or 
business.
    (B) Active conduct of a trade or business. For purposes of this 
paragraph (d)(3)(iv), whether, with respect to the trade or business at 
issue, the transferor and transferee are engaged in the active conduct 
of a trade or business is determined under Sec. 1.355-3(b)(2) and (3), 
except that--
    (1) Conduct is tested before the transfer (with respect to the 
transferor) and after the transfer (with respect to the transferee) 
rather than immediately after a distribution; and
    (2) The trade or business need not have been conducted for five 
years before its transfer, but it must have been conducted for a 
sufficient period of time to establish that it is a viable and ongoing 
trade or business.
    (C) Reasonable needs of the trade or business. For purposes of this 
paragraph (d)(3)(iv), the reasonable needs of the trade or business 
include only the amount of cash or cash items, marketable stock, or 
debt of the transferor that a prudent business person apprised of all 
relevant facts would consider necessary for the present and reasonably 
anticipated future needs of the business. Transferred items may be 
considered necessary for reasonably anticipated future needs only if 
the transferor and transferee have specific, definite, and feasible 
plans for their use. Those plans must require that items intended for 
anticipated future needs rather than present needs be used as 
expeditiously as possible consistent with the business purpose for 
retention of the items.
    Future needs are not reasonably anticipated if they are uncertain 
or vague or where the execution of the plan for their use is 
substantially postponed. The reasonable needs of a trade or business 
are generally its needs at the time of the transfer of the business 
including the items. However, for purposes of applying section 355(d) 
to a distribution, events and conditions after the transfer and through 
the date immediately after the distribution (including whether plans 
for the use of transferred items have been consummated or substantially 
postponed) may be considered to determine whether at the time of the 
transfer the items were necessary for the present and reasonably 
anticipated future needs of the business.
    (D) Consideration of all facts and circumstances. All facts and 
circumstances are considered in determining whether this paragraph 
(d)(3)(iv) applies.
    (v) Exception for transfer between members of the same affiliated 
group--(A) In general. Except to the extent provided in paragraph 
(e)(3) of this section, an acquisition of stock (whether actual or 
constructive) not described in paragraphs (d)(3)(iii) and (iv) of this 
section in exchange for any cash or cash item, marketable stock, or 
debt of the transferor in a section 351 transaction is not a purchase 
if the transferor corporation or corporations, the transferee 
corporation, and any distributed controlled corporation of the 
transferee corporation are members of the same affiliated group as 
defined in section 1504(a) before the section 351 transaction (if the 
transferee corporation is in existence before the transaction) and do 
not cease to be members of such affiliated group in any transaction 
that is related to the section 351 transaction (including any 
distribution of a controlled corporation by the transferee 
corporation). But see paragraph (b)(4) of this section where the 
transfer is made

[[Page 23566]]

for a principal purpose to avoid the purposes of section 355(d).
    (B) Examples. The following examples illustrate this paragraph 
(d)(3)(v):

    Example 1. Publicly traded P has wholly owned S since 1990. S is 
engaged in the business of computer software development and is 
developing a new software platform for use in the managed health 
care industry. Over a period of four years beginning on January 31, 
2000, P contributes a substantial amount of cash to S solely for the 
purpose of funding the software platform development. On completion 
of the software platform in January of 2004, 60 percent of the value 
of the S stock is attributable to the cash contributions made within 
the last four years. The P group's primary lender requires that S 
separately incorporate the software platform and related assets and 
distribute the new subsidiary to P as a condition of providing 
required funding to market the platform. Accordingly, on February 1, 
2004, S forms N, contributes the platform and related assets to N, 
and distributes all of the N stock to P in a transaction intended to 
qualify under section 355(a). P, S, and N will not leave the 
affiliated group in any transaction related to the cash 
contributions. Under paragraph (d)(3)(v)(A) of this section, P's 
cash contributions to S are not treated as purchases of additional S 
stock, and the distribution of N from S to P is not a disqualified 
distribution under section 355(d)(2) and paragraph (b)(1) of this 
section.
    Example 2. On Date 1, P contributes cash to its subsidiary S 
with a principal purpose to increase its stock basis in S. Sixty 
percent of the value of P's S stock is attributable to the cash 
contribution. Under paragraph (b)(4) of this section (anti-avoidance 
rule), 60 percent of the S stock is treated as purchased under 
section 355(d)(5)(B), notwithstanding paragraph (d)(3)(v)(A) of this 
section. Accordingly, any distribution of a subsidiary of S to P 
within the five-year period after Date 1 will be a disqualified 
distribution, regardless of whether P, S, and any distributed S 
subsidiary remain affiliated after the distribution and any 
transactions related to the cash contribution.

    (4) Triangular asset reorganizations--(i) Definition. A triangular 
asset reorganization is a reorganization that qualifies under--
    (A) Section 368(a)(1) (A) or (G) by reason of section 368(a)(2)(D);
    (B) Section 368(a)(1)(A) by reason of section 368(a)(2)(E) 
(regardless of whether section 368(a)(3)(E) applies), unless the 
transaction also qualifies as either a section 351 transfer or a 
reorganization under section 368(a)(1)(B); or
    (C) Section 368(a)(1)(C), and stock of the controlling corporation 
rather than the acquiring corporation is exchanged for the acquired 
corporation's properties.
    (ii) Treatment. Notwithstanding section 355(d)(5)(A), for purposes 
of section 355(d), the controlling corporation in a triangular asset 
reorganization is treated as having--
    (A) Acquired the assets of the acquired corporation (and as having 
assumed any liabilities assumed by the controlling corporation's 
subsidiary corporation or to which the acquired corporation's assets 
were subject (the acquired liabilities)) in a transaction in which the 
controlling corporation's basis in the acquired corporation's assets 
was determined under section 362(b); and
    (B) Transferred the acquired assets and acquired liabilities to its 
subsidiary corporation in a section 351 transfer.
    (iii) Example. The following example illustrates this paragraph 
(d)(4):

    Example. Forward triangular reorganization. P forms S with $10 
cash and T merges into S in a reorganization qualifying under 
section 368(a)(1)(A) by reason of section 368(a)(2)(D) in which the 
T shareholders receive solely P stock in exchange for their T stock. 
T is not a common parent of a consolidated group of corporations. 
The $10 cash with which P formed S will not be used in the acquired 
business. T's assets consist only of assets part of and used in its 
business with a value of $80, and $10 cash that is not part of or 
used in T's business. T has no liabilities. S will use T's business 
assets in T's business (which will become S's business), but will 
invest the $20 cash in an unrelated passive investment. Under 
paragraph (d)(4)(ii) of this section, P is treated as acquiring the 
T assets in a transaction in which P's basis in the T assets was 
determined under section 362(b) and contributing them to S in a 
section 351 transfer. The exception in paragraph (d)(3)(v) of this 
section does not apply because P and S became affiliated in the same 
transaction in which the section 351 transfer is deemed to occur. 
Accordingly, P is treated under section 355(d)(5)(B) and paragraph 
(d)(3)(iv) of this section as having purchased $20 of the S stock, 
but is not deemed to have purchased the remaining $80 of the S 
stock.

    (5) Reverse triangular reorganizations other than triangular asset 
reorganizations--(i) In general. Except as provided in paragraph 
(d)(5)(ii) of this section, if a transaction qualifies as a 
reorganization under section 368(a)(1)(A) by reason of section 
368(a)(2)(E) and also as either a reorganization under section 
368(a)(1)(B) or a section 351 transfer, then either section 
355(d)(5)(B) (and paragraph (d)(3) (i) through (iv) of this section) or 
355(d)(5)(C) (and paragraph (e)(2) of this section) applies. Regardless 
of which method the controlling corporation employs to determine its 
basis in the surviving corporation stock under Sec. 1.358-6(c)(2)(ii) 
or 1.1502-30(b), the total amount of surviving corporation stock 
treated as purchased by the controlling corporation will equal the 
higher of--
    (A) The amount of surviving corporation stock that would be treated 
as purchased (on the date of the deemed section 351 transfer) by the 
controlling corporation if the controlling corporation acquired the 
surviving corporation's assets and assumed its liabilities in a 
transaction in which the controlling corporation's basis in the 
surviving corporation assets was determined under section 362(b), and 
then transferred the acquired assets and liabilities to the surviving 
corporation in a section 351 transfer (see Secs. 1.358-6(c) (1) and 
(2)(ii)(A) and 1.1502-30(b)); or
    (B) The amount of surviving corporation stock that would be treated 
as purchased (on the date the surviving corporation shareholders 
purchased their surviving corporation stock) if the controlling 
corporation acquired the stock of the surviving corporation in a 
transaction in which the basis in the surviving corporation's stock was 
determined under section 362(b) (see Secs. 1.358-6(c)(2)(ii)(B) and 
1.1502-30(b)).
    (ii) Letter ruling and closing agreement. If a controlling 
corporation obtains a letter ruling and enters into a closing agreement 
under section 7121 in which it agrees to determine its basis in 
surviving corporation stock under Sec. 1.358-6(c)(2)(ii)(A), or under 
Sec. 1.1502-30(b) by applying Sec. 1.358-6(c)(2)(ii)(A) (deemed asset 
acquisition and transfer by controlling corporation), then section 
355(d)(5)(B) and paragraph (d)(3) (i) through (iv) of this section 
apply, and section 355 (d)(5)(C) and paragraph (e)(2) of this section 
do not apply. If a controlling corporation obtains a letter ruling and 
enters into a closing agreement under section 7121 under which it 
agrees to determine its basis in surviving corporation stock under 
Sec. 1.358-6(c)(2)(ii)(B), or under Sec. 1.1502-30(b) by applying 
1.358-6(c)(2)(ii)(B) (deemed stock acquisition), then section 355 
(d)(5)(C) and paragraph (e)(2) of this section apply, and section 355 
(d)(5)(B) and paragraphs (d)(3) (i) through (iv) of this section do not 
apply.
    (iii) Example. The following example illustrates this paragraph 
(d)(5):

    Example. Reverse triangular reorganization; purchase. (i) A 
purchases 60 percent of the stock of D on Date 1. D owns no cash 
items, marketable stock, or transferor debt, but holds cash that is 
not part of or used in D's trade or business under paragraph 
(d)(3)(iv) of this section and that represents 20 percent of D's 
value. On Date 2, P forms S, and S merges into D in a reorganization 
qualifying under section 368(a)(1)(B) and under section 368(a)(1)(A) 
by reason of section 368(a)(2)(E). In the reorganization, P acquires 
all of the D stock in exchange solely for P stock. After Date 2, and 
within five years after Date 1, D

[[Page 23567]]

distributes its wholly owned subsidiary C to P. P does not obtain a 
letter ruling and enter into a closing agreement under paragraph 
(d)(5)(ii) of this section. P would acquire 20 percent of the D 
stock by purchase on Date 2 under paragraph (d)(5)(i)(A) of this 
section by operation of section 355(d)(5)(B) and paragraph 
(d)(3)(iv) of this section. The exception in paragraph (d)(3)(v) of 
this section does not apply because P and S became affiliated in the 
same transaction in which the section 351 transfer is deemed to 
occur. P would acquire 60 percent of the D stock by purchase on Date 
1 under paragraph (d)(5)(i)(B) of this section because, under the 
transferred basis rule of section 355(d)(5)(C) and paragraph (e)(2) 
of this section, P is treated as though P purchased the D stock on 
the date A purchased it. Accordingly, under paragraph (d)(5)(i) of 
this section, P is treated as acquiring the higher amount (60 
percent) by purchase on Date 1. D's distribution of C to P is a 
disqualified distribution under section 355(d)(2) and paragraph 
(b)(1) of this section. In addition, A is treated as acquiring the P 
stock by purchase on Date 1 under paragraph (e)(3) of this section 
because A's basis in the P stock is determined by reference to A's 
basis in the D stock.
    (ii) The facts are the same as in paragraph (i) of this Example, 
except that P obtains a letter ruling and enters into a closing 
agreement under which it agrees to determine its basis in the D 
stock under Sec. 1.358-6(c)(2)(ii)(A). Under paragraph (d)(5)(ii) of 
this section, section 355(d)(5)(B) (and paragraphs (d)(3) (i) 
through (iv) of this section) applies, and section 355(d)(5)(C) (and 
paragraph (e)(2) of this section) does not apply. Accordingly, P is 
treated as acquiring only 20 percent of the D stock by purchase on 
Date 2. D's distribution of C to P is not a disqualified 
distribution under section 355(d)(2) and paragraph (b)(1) of this 
section.

    (6) Treatment of group structure changes--(i) In general. 
Notwithstanding section 355(d)(5)(A), for purposes of section 355(d), 
if a corporation succeeds another corporation as the common parent of a 
consolidated group in a group structure change to which Sec. 1.1502-31 
applies, the new common parent is treated as having acquired the assets 
and assumed the liabilities of the former common parent in a 
transaction in which the new common parent's basis in the former common 
parent's assets was determined under section 362(b), and then 
transferred the acquired assets and liabilities to the former common 
parent (or, if the former common parent does not survive, to the new 
common parent's subsidiary) in a section 351 transfer, with the new 
common parent and former common parent being treated as not in the same 
affiliated group at the time of the transfer (notwithstanding 
Sec. 1.1502-31(c)(2)).
    (ii) Adjustments to basis of higher-tier members. A higher-tier 
member that indirectly owns all or part of the former common parent's 
stock after a group structure change is treated as having purchased the 
stock of an immediate subsidiary to the extent that the higher-tier 
member's basis in the subsidiary is increased under Sec. 1.1502-
31(d)(4).
    (iii) Example. The following example illustrates this paragraph 
(d)(6):

    Example. P is the common parent of a consolidated group, and T 
is the common parent of another group. P has owned S for more than 
five years, and the fair market value of the S stock is $50. T's 
assets consist only of non-marketable stock of direct and indirect 
wholly owned subsidiaries with a value of $50, assets used in its 
business with a value of $50, and $50 of marketable stock that is 
not part of or used in T's business. T has no liabilities. T merges 
into S with the T shareholders receiving solely P stock with a value 
of $150 in exchange for their T stock in a section 368(a)(2)(D) 
reorganization. S will use T's business assets in T's business 
(which will become S's business), but will hold the $50 of 
marketable stock for investment purposes. Assume that the 
transaction is a reverse acquisition under Sec. 1.1502-75(d)(3) 
because the T shareholders, as a result of owning T stock, own more 
than 50 percent of the value of P's stock immediately after the 
transaction. Thus, the transaction is a group structure change under 
Sec. 1.1502-33(f)(1). Under paragraph (d)(6) of this section, P is 
treated as having acquired the assets of T in a transaction in which 
P's basis in the T assets was determined under section 362(b), and 
then transferred the acquired assets to S in a section 351 transfer, 
with P and T being treated as not in the same affiliated group at 
the time of the transfer. The exception in paragraph (d)(3)(v) of 
this section (transfers within an affiliated group) does not apply. 
Accordingly, P is treated under section 355(d)(5)(B) and paragraph 
(d)(3)(iv) of this section as having purchased $50 of the S stock 
(attributable to the marketable stock), but is not deemed to have 
purchased the remaining $150 of the S stock.

    (7) Special rules for triangular asset reorganizations, other 
reverse triangular reorganizations, and group structure changes. The 
amount of acquiring subsidiary, surviving corporation, or former common 
parent stock that is treated as purchased under paragraph (c)(4), 
(5)(i)(A), or (6) of this section (by operation of section 355(d)(5)(B) 
and paragraphs (d)(3) (i) through (iv) of this section) is adjusted to 
reflect any basis adjustment under--
    (i) Section 1.358-6(c)(2)(i) (B) and (C) (reduction of basis 
adjustment in reverse triangular reorganization where controlling 
corporation acquires less than all of the surviving corporation stock), 
Sec. 1.1502-30(b) (applying Sec. 1.358-6(c)(2)(i) (B) and (C) to a 
consolidated group), and Sec. 1.1502-31(d)(2)(ii) (reduction of basis 
adjustment in group structure change where new common parent acquires 
less than all of the former common parent stock); or
    (ii) Section 1.358-6(d) (reduction of basis adjustment in any 
triangular reorganization to the extent controlling corporation does 
not provide consideration), Sec. 1.1502-30(b) (applying Sec. 1.358-6(d) 
(except Sec. 1.358-6(d)(2)) to a consolidated group), and Sec. 1.1502-
31(d)(1) (reduction of basis adjustment in group structure change to 
the extent new common parent does not provide consideration).
    (e) Deemed purchase and timing rules--(1) Attribution and 
aggregation--(i) In general. Under section 355(d)(8)(B), if any person 
acquires by purchase an interest in any entity, and the person is 
treated under section 355(d)(8)(A) as holding any stock by reason of 
holding the interest, the stock shall be treated as acquired by 
purchase on the later of the date of the purchase of the interest in 
the entity or the date the stock is acquired by purchase by such 
entity.
    (ii) Purchase of additional interest. If a person and an entity are 
treated as a single person under section 355(d)(7), and the person 
later purchases an additional interest in the entity, the person is 
treated as purchasing on the date of the later purchase the amount of 
stock attributed from the entity to the person under section 
355(d)(8)(A) as a result of the additional interest.
    (iii) Purchase between persons treated as one person. If two 
persons are treated as one person under section 355(d)(7), and one 
later purchases stock or securities from the other, the date of the 
later purchase is used for purposes of determining when the five-year 
period commences.
    (iv) Purchase by a person already treated as holding stock under 
section 355(d)(8)(A). If a person who is already treated as holding 
stock under section 355(d)(8)(A) later directly purchases such stock, 
the date of the later direct purchase is used for purposes of 
determining when the five-year period commences.
    (v) Examples. The following examples illustrate this paragraph 
(e)(1):

    Example 1. On Date 1, A purchases 10 percent of the stock of P, 
which has held 100 percent of the stock of T for more than five 
years at the time of A's purchase. A is deemed to have purchased 10 
percent of P's T stock on Date 1. If A later purchases an additional 
41 percent of the stock of P on Date 2, A is deemed to have 
purchased an additional 41 percent of P's T stock on Date 2. Because 
A and P are now related persons under section 267(b), they are 
treated as one person under section 355(d)(7)(A), and A is treated 
as owning all of P's T stock. A is treated as acquiring 51 percent 
of the T stock by purchase at the times of A's respective purchases 
of P stock on Date 1 and Date 2. The remaining 49 percent of T stock 
is

[[Page 23568]]

treated as acquired when P acquired the T stock, more than five 
years before Date 1. If P distributes T within five years after Date 
1, the distribution will be a disqualified distribution under 
section 355 (d)(2) and paragraph (b)(1) of this section.
    Example 2. A has owned 60 percent of the stock of P for more 
than five years, and P has owned 40 percent of the stock of T for 
more than five years. A and P are treated as one person, and A is 
treated as owning 40 percent of the stock of T for more than five 
years. If P later purchases an additional 20 percent of the stock of 
T on Date 1, A is treated as acquiring by purchase the additional 20 
percent of T stock on Date 1. If A then purchases an additional 10 
percent of the stock of P on Date 2, under the attribution rule and 
the deemed purchase rule, A is deemed to have purchased on Date 2 an 
additional four percent of the T stock (10 percent of the 40 percent 
that P originally owned). In addition, even though A and P were 
already treated as one person under section 355(d)(7)(A), A is also 
deemed to have purchased two percent of the T stock on Date 2 (10 
percent of the 20 percent of the T stock that it was treated as 
purchasing on Date 1). A is still treated as owning all 60 percent 
of the T stock owned by P. However, of the 60 percent, A is treated 
as having purchased 18 percent of the T stock on Date 1 and 6 
percent of the T stock on Date 2, for a total of 24 percent 
purchased stock.
    Example 3. A purchases a 20 percent interest in partnership M on 
Date 1. M has owned 30 percent of the stock and 25 percent of the 
securities of P for more than five years. P has owned 40 percent of 
the stock and 100 percent of the securities of T for more than five 
years. Under section 318(a)(2)(C) as modified by section 
355(d)(8)(A), M is deemed to own 12 percent of the stock (30 percent 
of the 40 percent P owns) and 30 percent of the securities (30 
percent of the 100 percent P owns) of T. Under sections 318(a)(2)(A) 
and 355(d)(8)(B), A is deemed to have purchased 2.4 percent of the 
stock (20 percent of the 12 percent M is deemed to own) and 6 
percent of the securities (20 percent of the 30 percent M is deemed 
to own) of T on Date 1. Similarly, A is deemed to have purchased 6 
percent of the stock (20 percent of the 30 percent M owns) and five 
percent of the securities (20 percent of the 25 percent M owns) of P 
on Date 1. If M later purchases an additional 10 percent of P stock 
on Date 2, M is deemed to have purchased four percent of the stock 
(10 percent of the 40 percent P owns) and 10 percent of the 
securities (10 percent of the 100 percent P owns) of T on Date 2. A 
is deemed to have purchased two percent of the stock of P on Date 2 
(20 percent of the 10 percent M purchased). A is also deemed to have 
purchased 0.8 percent of the stock (20 percent of the four percent M 
is deemed to have purchased) and two percent of the securities (20 
percent of the 10 percent M is deemed to have purchased) of T on 
Date 2.
    Example 4. A and B are brother and sister. For more than five 
years, A has owned 75 percent of the stock of P, and B has owned 25 
percent of the stock of P. A and B are treated as one person under 
section 267(b), and the stock of each is treated as purchased on the 
date it was purchased by A and B, respectively. If B later purchases 
50 percent of the P stock from A on Date 1, A and B are still 
treated as one person. However, the 50 percent of P stock that B 
purchased from A is treated as purchased on Date 1.

    (2) Transferred basis rule. If any person acquires property from 
another person who acquired the property by purchase (determined with 
regard to section 355(d)(5) and paragraphs (d) and (e)(2) and (3) of 
this section, but without regard to section 355(d)(8) and paragraph 
(e)(1) of this section), and the adjusted basis of the property in the 
hands of the acquirer is determined in whole or in part by reference to 
the adjusted basis of the property in the hands of the other person, 
the acquirer is treated as having acquired the property by purchase on 
the date it was so acquired by the other person. The rule in this 
paragraph (e)(2) applies, for example, where stock of a corporation 
acquired by purchase is subsequently acquired in a section 351 transfer 
or a reorganization qualifying under section 368(a)(1)(B), but does not 
apply if the stock of a former common parent is acquired in a group 
structure change to which Sec. 1.1502-31 applies. But see paragraph 
(d)(2)(i)(B)(2) of this section for situations where the stock is 
treated as purchased on the date of a transfer.
    (3) Exchanged basis rule--(i) In general. If any person acquires an 
interest in an entity (the first interest) by purchase (determined with 
regard to section 355(d)(5) and paragraphs (d) and (e)(2) and (3) of 
this section, but without regard to section 355(d)(8) and paragraph 
(e)(1) of this section), and the first interest is exchanged for an 
interest in another entity (the second interest) where the adjusted 
basis of the second interest is determined in whole or in part by 
reference to the adjusted basis of the first interest, then the second 
interest is treated as having been purchased on the date the first 
interest was purchased. The rule in this paragraph (e)(3) applies, for 
example, where stock of a corporation acquired by purchase is 
subsequently exchanged for other stock in a section 351, 354, or 
1036(a) exchange. But see paragraph (d)(2)(i)(A)(2) of this section for 
situations where the stock is treated as purchased on the date of an 
exchange or distribution.
    (ii) Example. The following example illustrates this paragraph 
(e)(3):

    Example. A purchases 50 percent of the stock of T on Date 1. On 
Date 2, T merges into D in a section 368(a)(1)(A) reorganization, 
with A exchanging all of the T stock solely for stock of D. Under 
section 358(a), A's basis in the D stock is determined by reference 
to the basis of the T stock it purchased. Accordingly, A is treated 
as having purchased the D stock on Date 1, and has a purchased basis 
in the D stock under paragraph (b)(3)(iii) of this section.

    (4) Substantial diminution of risk--(i) In general. If section 
355(d)(6) applies to any stock for any period, the running of any five-
year period set forth in section 355(d)(3) is suspended during such 
period.
    (ii) Property to which suspension applies. Section 355(d)(6) 
applies to any stock for any period during which the holder's risk of 
loss with respect to such stock, or with respect to any portion of the 
activities of the corporation, is (directly or indirectly) 
substantially diminished by an option, a short sale, any special class 
of stock, or any other device or transaction.
    (iii) Risk of loss substantially diminished. Whether a holder's 
risk of loss is substantially diminished under section 355(d)(6) and 
paragraph (e)(4)(ii) of this section will be determined based on all 
facts and circumstances relating to the stock, the corporate 
activities, and arrangements for holding the stock.
    (iv) Special class of stock. For purposes of section 355(d)(6) and 
paragraph (e)(4)(ii) of this section, the term special class of stock 
includes a class of stock that grants particular rights to, or bears 
particular risks for, the holder or the issuer with respect to the 
earnings, assets, or attributes of less than all the assets or 
activities of a corporation or any of its subsidiaries. The term 
includes, for example, tracking stock and stock (or any related 
instruments or arrangements) the terms of which provide for the 
distribution (whether or not at the option of any party or in the event 
of any contingency) of any controlled corporation or other specified 
assets to the holder or to one or more persons other than the holder.
    (f) Duty to determine stockholders--(1) In general. In determining 
whether section 355(d) applies to a distribution of controlled 
corporation stock, a distributing corporation must determine whether a 
disqualified person holds its stock or the stock of any distributed 
controlled corporation. This paragraph (f) provides rules regarding 
this determination and the extent to which a distributing corporation 
must investigate whether a disqualified person holds stock.
    (2) Deemed knowledge of contents of securities filings. A 
distributing corporation is deemed to have knowledge of the existence 
and contents of all schedules, forms, and other documents filed with or 
under the rules of the Securities and Exchange Commission, including 
without limitation any Schedule 13D or 13G (or

[[Page 23569]]

any similar schedules) and amendments, with respect to any relevant 
corporation.
    (3) Presumption as to securities filings. Absent actual knowledge 
to the contrary, in determining whether section 355(d) applies to a 
distribution, a distributing corporation may presume, with respect to 
stock that is reporting stock (while such stock is reporting stock), 
that every shareholder or other person required to file a schedule, 
form, or other document with or under the rules of the Securities and 
Exchange Commission as of a given date has filed the schedule, form, or 
other document as of that date and that the contents of filed 
schedules, forms, or other documents are accurate and complete. 
Reporting stock is stock that is described in Rule 13d-1(i) of 
Regulation 13D (17 CFR 240.13d-1(i)) (or any rule or regulation to 
generally the same effect) promulgated by the Securities and Exchange 
Commission under the Securities Exchange Act of 1934 (15 U.S.C. 78a et 
seq.).
    (4) Presumption as to less-than-five-percent shareholders. Absent 
actual knowledge (or deemed knowledge under paragraph (f)(2) of this 
section) immediately after the distribution to the contrary with regard 
to a particular shareholder, a distributing corporation may presume 
that no less-than-five-percent shareholder of a corporation acquired 
stock by purchase under section 355(d) (5) or (8) and paragraphs (d) 
and (e) of this section during the five-year period. For purposes of 
this paragraph (f), a less-than-five-percent shareholder is a person 
that, at no time during the five-year period, holds directly (or by 
application of paragraph (c)(3)(ii) of this section, but not by 
application of section 355(d) (7) or (8)) stock possessing five percent 
or more of the total combined voting power of all classes of stock 
entitled to vote and the total value of shares of all classes of stock 
of a corporation. However, this presumption does not apply to any less-
than-five-percent shareholder that, at any time during the five-year 
period--
    (i) Is related under section 355(d)(7)(A) to a shareholder in the 
corporation that is, at any time during the five-year period, not a 
less-than-five-percent shareholder;
    (ii) Acted pursuant to a plan or arrangement, with respect to 
acquisitions of the corporation's stock under section 355 (d)(7)(B) and 
paragraph (c)(4) of this section, with a shareholder in the corporation 
that is, at any time during the five-year period, not a less-than-five-
percent shareholder; or
    (iii) Holds stock that is attributed under section 355(d)(8)(A) to 
a shareholder in the corporation that is, at any time during the five-
year period, not a less-than-five-percent shareholder.
    (5) Examples. The following examples illustrate this paragraph (f):

    Example 1. Publicly traded corporation; no schedules filed. D is 
a widely held and publicly traded corporation with a single class of 
reporting stock and no other class of stock. Assume that applicable 
federal law requires any person that directly holds five percent or 
more of the D stock to file a schedule with the Securities and 
Exchange Commission within 10 days after an acquisition. D 
distributes its wholly owned subsidiary C pro rata. D determines 
that no schedule, form, or other document has been filed with 
respect to its stock or the stock of any other relevant corporation 
during the five-year period or within 10 days after the 
distribution. Immediately after the distribution, D has no knowledge 
that any of its shareholders are (or were at any time during the 
five-year period) not less-than-five-percent shareholders, or that 
any particular shareholder acquired D stock by purchase under 
section 355(d) (5) or (8) and paragraphs (d) and (e) of this section 
during the five-year period. Under paragraph (f)(3) of this section, 
D may presume it has no shareholder that is or was not a less-than-
five-percent shareholder during the five-year period due to the 
absence of any filed schedules, forms, or other documents. Under 
paragraph (f)(4) of this section, D may presume that none of its 
less-than-five-percent shareholders acquired D's stock by purchase 
during the five-year period. Accordingly, D may presume that section 
355(d) does not apply to the distribution of C.
    Example 2. Publicly traded corporation; schedule filed. The 
facts are the same as those in Example 1, except that D determines 
that, as of 10 days after the distribution, only one schedule has 
been filed with respect to its stock. That schedule discloses that X 
acquired 15 percent of the D stock one year before the distribution. 
Absent contrary knowledge, D may rely on the presumptions in 
paragraph (f)(3) of this section and so may presume that X is its 
only shareholder that is or was not a less-than-five-percent 
shareholder during the five-year period. D may not rely on the 
presumption in paragraph (f)(4) of this section with respect to X. 
In addition, D may not rely on the presumption in paragraph (f)(4) 
of this section with respect to any less-than-five-percent 
shareholder that, at any time during the five-year period, is 
related to X under section 355(d)(7)(A), acted pursuant to a plan or 
arrangement with X under section 355 (d)(7)(B) and paragraph (c)(4) 
of this section with respect to acquisitions of D stock, or holds 
stock that is attributed to X under section 355(d)(8)(A). 
Accordingly, under paragraph (f)(1) of this section, to determine 
whether section 355(d) applies, D must determine: whether X acquired 
its directly held D stock by purchase under section 355(d)(5) and 
paragraphs (d) and (e)(2) and (3) of this section during the five-
year period; whether X is treated as having purchased any additional 
D stock under section 355 (d)(8) and paragraph (e)(1) of this 
section during the five-year period; and whether X is related to, or 
acquired its D stock pursuant to a plan or arrangement with, one or 
more of D's other shareholders during the five-year period under 
section 355(d)(7) (A) or (B) and paragraph (c)(4) of this section, 
and if so, whether those shareholders acquired their D stock by 
purchase under section 355(d) (5) or (8) and paragraphs (d) and (e) 
of this section during the five-year period.
    Example 3. Acquisition of publicly traded corporation. The facts 
are the same as those in Example 1, except that P acquires all of 
the D stock in a section 368(a)(1)(B) reorganization that is not 
also a reorganization under section 368(a)(1)(A) by reason of 
section 368(a)(2)(E), and D distributes C to P one year later. Under 
the deemed purchase rule of section 355 (d)(5)(C) and paragraph 
(e)(2) of this section, P is treated as having acquired the D stock 
by purchase on the date the D shareholders acquired the D stock by 
purchase. Even though D has no less-than-five-percent shareholder 
immediately after the distribution, D may rely on the presumptions 
in paragraphs (f)(3) and (4) of this section to determine whether 
and to what extent the D stock is treated as purchased during the 
five-year period in P's hands under the deemed purchase rule of 
section 355 (d)(5)(C) and paragraph (e)(2) of this section. 
Accordingly, D may presume that section 355(d) does not apply to the 
distribution of C to P.
    Example 4. Non-publicly traded corporation. D is owned by 20 
shareholders and has a single class of stock that is not reporting 
stock. D knows that A owns 40 percent of the D stock, and D does not 
know that any other shareholder has owned as much as five percent of 
the D stock at any time during the five-year period. D may not rely 
on the presumption in paragraph (f)(3) of this section because its 
stock is not reporting stock. D may not rely on the presumption in 
paragraph (f)(4) of this section with respect to A. In addition, D 
may not rely on the presumption in paragraph (f)(4) of this section 
for any less-than-five-percent shareholder that, at any time during 
the five-year period, is related to A under section 355(d)(7)(A), 
acted pursuant to a plan or arrangement with A under section 355 
(d)(7)(B) and paragraph (c)(4) of this section with respect to 
acquisitions of D stock, or holds stock that is attributed to A 
under section 355(d)(8)(A). D may rely on the presumption in 
paragraph (f)(4) of this section for less-than-five-percent 
shareholders that during the five-year period are not related to A, 
did not act pursuant to a plan or arrangement with A, and do not 
hold stock attributed to A. Accordingly, under paragraph (f)(1) of 
this section, to determine whether section 355(d) applies, D must 
determine: that A is its only shareholder that is (or was at any 
time during the five-year period) not a less-than-five-percent 
shareholder; whether A acquired its directly held D stock by 
purchase under section 355 (d)(5) and paragraphs (d) and (e)(2) and 
(3) of this section during the five-year period; whether A is 
treated as having purchased any additional D stock under section 355 
(d)(8) and paragraph (e)(1) of this

[[Page 23570]]

section during the five-year period; and whether A is related to, or 
acquired its D stock pursuant to a plan or arrangement with, one or 
more of D's other shareholders during the five-year period under 
section 355(d)(7) (A) or (B) and paragraph (c)(4) of this section, 
and if so, whether those shareholders acquired their D stock by 
purchase under section 355(d) (5) or (8) and paragraphs (d) and (e) 
of this section during the five-year period.

    (g) Effective date. The regulations in this section apply to 
distributions occurring after the regulations in this section are 
published as final regulations in the Federal Register, except that 
they do not apply to any distributions occurring pursuant to a written 
agreement which is (subject to customary conditions) binding on the 
date the regulations in this section are published as final regulations 
in the Federal Register, and at all times thereafter.
Robert E. Wenzel,
Deputy Commissioner of Internal Revenue.
[FR Doc. 99-10818 Filed 4-29-99; 8:45 am]
BILLING CODE 4830-01-P