Reg. § 1.409(p)-1T Prohibited allocations of securities in an S corporation (temporary).
(a) Organization of this section Section applies if a nonallocation year occurs in an employee stock ownership plan (ESOP), as defined in section , that holds shares of stock of an S corporation, as defined in section , that are employer securities as defined in section . of this section sets forth the general rule under section and (2) prohibiting any accrual or allocation to a disqualified person in a nonallocation year. of this section sets forth rules under section , (5), and (7) for determining whether a year is a nonallocation year, generally based on whether disqualified persons own at least 50 percent of the shares of the S corporation, either taking into account only the outstanding shares of the S corporation (including shares held by the ESOP) or taking into account both the outstanding shares and synthetic equity of the S corporation. , , and of this section contain definitions of disqualified person under section and (5), deemed-owned ESOP shares under section , and synthetic equity under section . of this section contains a standard for determining when the principal purpose of the ownership structure of an S corporation constitutes an avoidance or evasion of section . The definitions used in section and this section are also applicable for purposes of section , which imposes an excise tax on certain events, including a nonallocation year under section .
(b) Prohibited allocation in a nonallocation year
(1) General rule An ESOP holding employer securities consisting of stock in an S corporation must provide that no portion of the assets of the plan attributable to (or allocable in lieu of) such employer securities may, during a nonallocation year, accrue under the ESOP, or be allocated directly or indirectly under any plan of the employer (including the ESOP) meeting the requirements of section , for the benefit of any disqualified person (a prohibited allocation).
(2) Additional rules
(i) Prohibited allocation definition For purposes of section and of this section, there is a prohibited allocation (i.e., assets accrue or are allocated as prohibited under of this section) if there is either an impermissible accrual as defined in of this section or an impermissible allocation as defined in of this section. The amount of the prohibited allocation is equal to the sum of the impermissible accrual plus the amount of the impermissible allocation (if any).
(ii) Impermissible accrual There is an impermissible accrual to the extent (and only to the extent) that employer securities consisting of stock in an S corporation owned by the ESOP and any assets attributable thereto are held under the ESOP for the benefit of a disqualified person during a nonallocation year. For this purpose, assets attributable to S corporation securities include any distributions, within the meaning of section , made on S corporation stock held in a disqualified person's account in the ESOP (including earnings thereon), plus any proceeds from the sale of S corporation securities held for a disqualified person's account in the ESOP (including any earnings thereon). Thus, for example, in the event of a nonallocation year, all S corporation shares and all other ESOP assets attributable to S corporation stock, including distributions, sales proceeds, and earnings on either the distribution or proceeds, held for the account of such disqualified person in the ESOP during that year are an impermissible accrual for the benefit of that person, whether attributable to contributions in the current year or in prior years.
(iii) Impermissible allocation An impermissible allocation means any allocation for a disqualified person directly or indirectly under any plan of the employer qualified under section that occurs during a nonallocation year to the extent that a contribution or other annual addition is made, or the disqualified person otherwise accrues additional benefits, under the ESOP or any other plan of the employer qualified under section (including a release and allocation of assets from a suspense account, as described at and ) that, for the nonallocation year, would otherwise have been added to the account of the disqualified person under the ESOP and invested in employer securities consisting of stock in an S corporation owned by the ESOP but for a provision in the ESOP to comply with section .
(iv) Effects of prohibited allocation
(A) Deemed distribution If there is a prohibited allocation, the amount of the prohibited allocation, as determined under this , is treated as distributed from the ESOP (or other plan of the employer) to the disqualified person on the first day of the plan year on which there is an impermissible accrual or on the date of the allocation in the case of an additional impermissible accrual or impermissible allocation during the plan year but after the first day of the plan year. Thus, the fair market value of assets in the disqualified person's account that constitutes an impermissible accrual or allocation is included in gross income (to the extent in excess of any investment in the contract allocable to such amount) and is subject to any additional income tax that applies under section . A deemed distribution under this is not an actual distribution from the ESOP. Thus, the amount of the prohibited allocation is not an eligible rollover distribution under section . However, for purposes of applying sections and with respect to any subsequent distribution from the ESOP, the amount that the disqualified person previously took into account as income as a result of the deemed distribution is treated as an investment in the contract.
(B) Other effects If there is a prohibited allocation, then the plan fails to satisfy the requirements of section and ceases to be an ESOP. In such a case, the exemption from the excise tax on prohibited transactions for loans to leveraged ESOPs contained in section would cease to apply to any loan (with the result that the employer would owe an excise tax with respect to the previously exempt loan) and, further, the exception in section would not apply to the plan (with the result that the plan may owe income tax as a result of unrelated business taxable income under section with respect to S corporation stock held by the plan). See also section which imposes an excise tax in certain events, including a prohibited allocation under section .
(v) Prevention of prohibited allocation
(A) Transfer of account to non-ESOP An ESOP may prevent a nonallocation year or a prohibited allocation during a nonallocation year by permitting assets (including S corporation securities) allocated to the account of a disqualified person (or a person reasonably expected to become a disqualified person absent a transfer described in this ) to be transferred into a separate portion of the plan that is not an ESOP, as described in , or to another plan of the employer that satisfies the requirements of section (and that is not an ESOP). In the event of such a transfer involving S corporation securities, the recipient plan is subject to tax on unrelated business taxable income under section .
(B) Relief from nondiscrimination requirement Pursuant to this , if a transfer described in of this section is made from an ESOP to a separate portion of the plan or to another qualified plan of the employer that is not an ESOP, then both the ESOP and the plan or portion of a plan that is not an ESOP will not fail to satisfy the requirements of merely because of the transfer. Further, subsequent to the transfer, that plan will not fail to satisfy the requirements of merely because of the benefits, rights, or features with respect to the transferred benefits if those benefits, rights, or features would satisfy the requirements of if the mandatory disaggregation rule for ESOPs at did not apply.
(c) Nonallocation year
(1) Definition generally For purposes of section and this section, a nonallocation year means a plan year of an ESOP during which, at any time, the ESOP holds any employer securities that are shares of an S corporation and either—
(i) Disqualified persons own at least 50 percent of the number of outstanding shares of stock in the S corporation (including deemed-owned ESOP shares); or
(ii) Disqualified persons own at least 50 percent of the sum of:
(A) The outstanding shares of stock in the S corporation (including deemed-owned ESOP shares), plus
(B) The shares of synthetic equity in the S corporation owned by disqualified persons.
(2) Attribution rules For purposes of this , the rules of section apply to determine ownership of shares in the S corporation (including deemed-owned ESOP shares) and synthetic equity. However, for this purpose, section (relating to options to acquire stock) is disregarded and, in applying section , the members of an individual's family include members of the individual's family under of this section. In addition, an individual is treated as owning deemed-owned ESOP shares of that individual notwithstanding the employee trust exception in section . If the attribution rules in of this section apply, then the rules of of this section are applied before the rules of this .
(3) Special rule for avoidance or evasion
(i) The ownership structures described in of this section result in a nonallocation year. In addition, under the ownership structures described in of this section, the individual referred to in of this section is treated as a disqualified person and that person's interest in the separate entity is treated as synthetic equity.
(ii) Under section , the Commissioner, in revenue rulings, notices, and other guidance published in the Internal Revenue Bulletin (see ), may provide that a nonallocation year occurs in any case in which the principal purpose of the ownership structure of an S corporation constitutes an avoidance or evasion of section . For any year that is a nonallocation year under this , the Commissioner may treat any person as a disqualified person. See of this section for guidance regarding when the principal purpose of an ownership structure of an S corporation involving synthetic equity constitutes an avoidance or evasion of section .
(4) Special rule for certain stock rights
(i) For purposes of of this section, a person is treated as owning stock that the person has a right to acquire if, at all times during the period when such right is effective, the stock that the person has the right to acquire is both issued and outstanding and is held by persons other than the ESOP, the S corporation, or a related entity (as defined in of this section).
(ii) This applies only if treating persons as owning the shares described in of this section results in a nonallocation year. This does not apply to a right to acquire stock of an S corporation held by a shareholder subject to Federal income tax that, under or , would not be taken into account in determining if an S corporation has a second class of stock provided that a principal purpose of the right is not the avoidance or evasion of section . Under the last sentence of of this section, this does not apply for purposes of determining ownership of deemed-owned ESOP shares or whether an interest constitutes synthetic equity.
(5) Application with respect to shares treated as owned by more than one person For purposes of applying of this section, if, by application of the rules of , , or of this section, any share is treated as owned by more than one person, then that share is counted as a single share and that share is treated as owned by disqualified persons if any of the owners is a disqualified person.
(6) Effect of nonallocation year See of this section for a prohibition applicable during a nonallocation year. See also section for an excise tax applicable in certain cases, including section and (4) which applies during a nonallocation year (whether or not there is a prohibited allocation during the year).
(d) Disqualified persons
(1) General definition For purposes of section and this section, a disqualified person means any person for whom—
(i) The number of such person's deemed-owned ESOP shares of the S corporation is at least 10 percent of the number of the deemed-owned ESOP shares of the S corporation;
(ii) The aggregate number of such person's deemed-owned ESOP shares and synthetic equity shares of the S corporation is at least 10 percent of the sum of:
(A) The total number of deemed-owned ESOP shares; and
(B) The person's synthetic equity shares of the S corporation;
(iii) The aggregate number of the S corporation's deemed-owned ESOP shares of such person and of the members of such person's family is at least 20 percent of the number of deemed-owned ESOP shares of the S corporation; or
(iv) The aggregate number of the S corporation's deemed-owned ESOP shares and synthetic equity shares of such person and of the members of such person's family is at least 20 percent of the sum of:
(A) The total number of deemed-owned ESOP shares, and
(B) The synthetic equity shares of the S corporation owned by such person and the members of such person's family.
(2) Treatment of family members; definition
(i) Rule Each member of the family of any person who is a disqualified person under or of this section is a disqualified person.
(ii) General definition For purposes of section and this section, member of the family means, with respect to an individual—
(A) The spouse of the individual;
(B) An ancestor or lineal descendant of the individual or the individual's spouse;
(C) A brother or sister of the individual or of the individual's spouse and any lineal descendant of the brother or sister; and
(D) The spouse of any individual described in or of this section.
(iii) Spouse A spouse of an individual who is legally separated from such individual under a decree of divorce or separate maintenance is not treated as such individual's spouse under of this section.
(3) Special rule for certain nonallocation years See of this section (relating to avoidance or evasion of section ) for special rules permitting certain persons to be treated as disqualified persons in certain nonallocation years.
(4) Example The rules of this are illustrated by the following example:
Example.
(i) Facts. An S corporation has 800 outstanding shares of which 100 are owned by individual O and 700 are held in an employee stock ownership plan (ESOP) during 2005, including 200 shares held in the ESOP account of O, 65 shares held in the ESOP account of participant P, and 40 shares held in the ESOP account of participant Q who is P's spouse. The S corporation has no synthetic equity.
(ii) Conclusion. O is a disqualified person during 2005 because O's account in the ESOP holds at least 10 percent of the shares owned by the ESOP (200 is 28.6 percent of 700). In addition, P is a disqualified person during 2005 because, under of this section, P is treated as owning the shares held by Q and P's total deemed-owned shares are thus at least 10 percent of the shares owned by the plan (65 plus 40 is more than 10 percent of 700). In addition, Q is a disqualified person as a result of the rules in of this section. As a result, disqualified persons own at least 50 percent of the outstanding shares of the S corporation during 2005 (O's 100 directly owned shares, O's 200 deemed-owned shares, P's 65 deemed-owned shares, plus Q's 40 deemed owned shares are 50.6 percent of 800).
(e) Deemed-owned ESOP shares For purposes of section and this section, a person is treated as owning his or her deemed-owned ESOP shares.
(f) Synthetic equity
(1) Ownership of synthetic equity For purposes of section and this section, synthetic equity is treated as owned by a person in the same manner as stock is treated as owned by a person, directly or under the rules of section and (3). Synthetic equity means the rights described in of this section.
(2) Synthetic equity
(i) Rights to acquire stock of the S corporation Synthetic equity includes any stock option, warrant, restricted stock, deferred issuance stock right, stock appreciation right payable in stock, or similar interest or right that gives the holder the right to acquire or receive stock of the S corporation in the future. Rights to acquire stock in an S corporation with respect to stock that is, at all times during the period when such rights are effective, both issued and outstanding and held by persons (who are subject to federal income taxes) other than the ESOP, the S corporation, or a related entity are not synthetic equity (but see of this section).
(ii) Special rule for certain stock rights. Synthetic equity also includes a right to a future payment (payable in cash or any other form other than stock of the S corporation) from an S corporation that is based on the value of the stock of the S corporation, such as appreciation in such value. Thus, synthetic equity includes a stock appreciation right with respect to stock of an S corporation that is payable in cash or a phantom stock unit with respect to stock of an S corporation that is payable in cash.
(iii) Rights to acquire interests in or assets of an S corporation or a related entity Synthetic equity includes a right to acquire stock or other similar interests in a related entity to the extent of the S corporation's ownership. Synthetic equity also includes a right to acquire assets of an S corporation or a related entity other than either rights to acquire goods, services, or property at fair market value in the ordinary course of business or fringe benefits excluded from gross income under section .
(iv) Special rule for nonqualified deferred compensation
(A) Synthetic equity also includes any of the following with respect to an S corporation or a related entity: any remuneration to which section applies; remuneration for which a deduction would be permitted under section if separate accounts were maintained; any right to receive property to which section applies (including a payment to a trust described in section or to an annuity described in section ) in a future year for the performance of services; any transfer of property (to which section applies) in connection with the performance of services to the extent that the property is not substantially vested within the meaning of by the end of the plan year in which transferred; and a split-dollar life insurance arrangement under entered into in connection with the performance of services (other than one under which, at all times, the only economic benefit that will be provided under the arrangement is current life insurance protection as described in ). Synthetic equity also includes any other remuneration for services under a plan, or method or arrangement, deferring the receipt of compensation to a date that is after the 15th day of the 3rd calendar month after the end of the entity's taxable year in which the related services are rendered. However, synthetic equity does not include benefits under a plan that is an eligible retirement plan within the meaning of section .
(B) For purposes of applying of this section with respect to an ESOP, synthetic equity does not include any interest described in such of this section to the extent that—
(1) The interest is nonqualified deferred compensation (within the meaning of section ) that was outstanding on December 17, 2004;
(2) The interest is an amount that was taken into account (within the meaning of ) prior to January 1, 2005, for purposes of taxation under chapter 21 of the Internal Revenue Code (or income attributable thereto); and
(3) The interest was held before the first date on which the ESOP acquires any employer securities.
(v) No overlap among shares of deemed-owned ESOP shares or synthetic equity Synthetic equity under this does not include shares that are deemed-owned ESOP shares (or any rights with respect to deemed-owned ESOP shares to the extent such rights are specifically permitted under section ). In addition, synthetic equity under a specific subparagraph of this does not include anything that is synthetic equity under , , or of this section.
(3) Related entity For purposes of this , related entity means any entity in which the S corporation holds an interest and which is a partnership, a trust, an eligible entity that is disregarded as an entity that is separate from its owner under , or a Qualified Subchapter S Subsidiary under section .
(4) Number of synthetic shares
(i) Synthetic equity determined by reference to S corporation shares In the case of synthetic equity that is determined by reference to shares of stock of the S corporation, the person who is entitled to the synthetic equity is treated as owning the number of shares of stock deliverable pursuant to such synthetic equity. In the case of synthetic equity that is determined by reference to shares of stock of the S corporation, but for which payment is made in cash or other property (besides stock of the S corporation), the number of shares of synthetic equity treated as owned is equal to the number of shares of stock having a fair market value equal to the cash or other property (disregarding lapse restrictions as described in ). Where such synthetic equity is a right to purchase or receive S corporation shares, the corresponding number of shares of synthetic equity is determined without regard to lapse restrictions as described in or to any amount required to be paid in exchange for the shares. Thus, for example, if a corporation grants an employee of an S corporation an option to purchase 100 shares of the corporation's stock, exercisable in the future only after the satisfaction of certain performance conditions, the employee is the deemed owner of 100 synthetic equity shares of the corporation as of the date the option is granted. If the same employee were granted 100 shares of restricted S corporation stock (or restricted stock units), subject to forfeiture until the satisfaction of performance or service conditions, the employee would likewise be the deemed owner of 100 synthetic equity shares from the grant date. However, if the same employee were granted a stock appreciation right with regard to 100 shares of S corporation stock (whether payable in stock or in cash), the number of synthetic equity shares the employee is deemed to own equals the number of shares having a value equal to the appreciation at the time of measurement (determined without regard to lapse restrictions).
(ii) Synthetic equity determined by reference to shares in a related entity In the case of synthetic equity that is determined by reference to shares of stock (or similar interests) in a related entity, the person who is entitled to the synthetic equity is treated as owning shares of stock of the S corporation with the same aggregate value as the number of shares of stock (or similar interests) of the related entity (with such value determined without regard to any lapse restriction as defined at ).
(iii) Other synthetic equity
(A) General rule In the case of any synthetic equity to which neither paragraph (f)(4)(i) nor of this section apply, the person who is entitled to the synthetic equity is treated as owning on any date a number of shares of stock in the S corporation equal to the present value (on that date) of the synthetic equity (with such value determined without regard to any lapse restriction as defined at ) divided by the fair market value of a share of the S corporation's stock as of that date.
(B) Special rules
(1) Use of annual or more frequent determination dates For purposes of this , while the determination of whether there is a nonallocation year depends on day-by-day determinations under of this section, the number of shares of S corporation stock treated as owned by a person who is entitled to synthetic equity to which this applies is permitted to be determined only annually (or more frequently), as of the first day of the ESOP's plan year or as of any other reasonable determination date or dates during a plan year. If the ESOP so provides, the number of shares of synthetic equity to which this applies that are treated as owned by that person for any period from a given determination date through the date immediately preceding the next following determination date is the number of shares treated as owned on the given determination date.
(2) Use of triannual recalculations In addition, if the terms of the ESOP so provide, then the number of shares of synthetic equity with respect to grants of synthetic equity to which this applies may be fixed for a specified period from a determination date identified under the ESOP through a date that is not later than the day before the determination date that is on or immediately preceding the third anniversary of the identified determination date. Additional accruals, allocations, or grants (to which this applies) that are made during such three-year period are taken into account on each determination date during that period, based on the number of synthetic equity shares resulting from the additional accrual, allocation, or grant (determined as of the determination date on or next following the date of the accrual, allocation, or grant). However, the ESOP must provide for the number of shares of synthetic equity to which this applies to be re-determined not less frequently than every three years, based on the S corporation share value on a determination date that is not later than the third anniversary of the identified determination date and the aggregate present value of the synthetic equity to which this applies (including all grants made during the three-year period) on that determination date. See Example 3 of of this section for an example illustrating this .
(3) Conditions for application of rules of this section only applies with respect to grants of synthetic equity to which this applies. In addition, of this section applies only if the fair market value of a share of the S corporation securities on any determination date is not unrepresentative of the value of the S corporation securities throughout the rest of the plan year and only if the terms of the ESOP include provisions conforming to of this section which are consistently used by the ESOP for all persons. In addition, of this section applies only if the terms of the ESOP include provisions conforming to and of this section which are consistently used by the ESOP for all persons.
(iv) Adjustment of number of synthetic equity shares where ESOP owns less than 100% of S corporation Under this , the number of synthetic shares otherwise determined under this is decreased ratably to the extent that shares of the S corporation are owned by a person who is not an ESOP (and who is subject to Federal income taxes). For example, if an S corporation has 200 outstanding shares, of which individual A owns 50 shares and the ESOP owns the other 150 shares, and individual B would be treated under this as owning 200 synthetic equity shares of the S corporation but for this , then, under the rule of this , the number of synthetic shares treated as owned by B under this is decreased from 200 to 150 (because the ESOP only owns 75% of the outstanding stock of the S corporation, rather than 100%).
(v) Special rule for shares with greater voting power than ESOP shares Notwithstanding any other provision of this , if a synthetic equity right includes (directly or indirectly) a right to purchase or receive shares of S corporation stock that have per-share voting rights greater than the per-share voting rights of one or more shares of S corporation stock held by the ESOP, then the number of shares of deemed owned synthetic equity attributable to such right is not less than the number of shares that would have the same voting rights if the shares had the same per-share voting rights as shares held by the ESOP with the least voting rights. For example, if shares of S corporation stock held by the ESOP have one voting right per share, then an individual who holds an option to purchase one share with 100 voting rights is treated as owning 100 shares of synthetic equity.
(g) Avoidance or evasion of section 409(p) involving synthetic equity
(1) General rule of this section sets forth a standard for determining whether the principal purpose of the ownership structure of an S corporation involving synthetic equity constitutes an avoidance or evasion of section . of this section identifies certain specific ownership structures that constitute an avoidance or evasion of section . See also of this section for a rule under which the ownership structures in paragraph (g)(3) result in a nonallocation year for purposes of section .
(2) Standard for determining when there is an avoidance or evasion of section 409(p) involving synthetic equity —For purposes of section and this section, whether the principal purpose of the ownership structure of an S corporation involving synthetic equity constitutes an avoidance or evasion of section is determined by taking into account all the surrounding facts and circumstances, including all features of the ownership of the S corporation's outstanding stock and related obligations (including synthetic equity), any shareholders who are taxable entities, and the cash distributions made to shareholders, to determine whether, to the extent of the ESOP's stock ownership, the ESOP receives the economic benefits of ownership in the S corporation that occur during the period that stock of the S corporation is owned by the ESOP. Among the factors indicating that the ESOP receives these economic benefits include shareholder voting rights, the right to receive distributions made to shareholders, and the right to benefit from the profits earned by the S corporation, including the extent to which actual distributions of profits are made from the S corporation to the ESOP and the extent to which the ESOP's ownership interest in undistributed profits and future profits is subject to dilution as a result of synthetic equity, for example, the ESOP's ownership interest is not subject to dilution if the total amount of synthetic equity is a relatively small portion of the total number of shares and deemed-owned shares of the S corporation.
(3) Specific transactions that constitute an avoidance or evasion of section 409(p) involving segregated profits Taking into account the standard in of this section, the principal purpose of the ownership structure of an S corporation constitutes an avoidance or evasion of section in any case in which—
(i) The profits of the S corporation generated by the business activities of a specific individual or individuals are not provided to the ESOP, but are instead substantially accumulated and held for the benefit of that individual or individuals on a tax-deferred basis within an entity related to the S corporation, such as a partnership, trust, or corporation (such as in a subsidiary that is a disregarded entity), or any other method that has the same effect of segregating profits for the benefit of such individual or individuals (such as nonqualified deferred compensation described in of this section);
(ii) The individual or individuals for whom profits are segregated have rights to acquire 50 percent or more of those profits directly or indirectly (for example, by purchase of the subsidiary); and
(iii) A nonallocation year would occur if this section were separately applied with respect to either the separate entity or whatever method has the effect of segregating profits of the individual or individuals, treating such entity as a separate S corporation owned by an ESOP (or in the case of any other method of segregation of profits by treating those profits as the only assets of a separate S corporation owned by an ESOP).
(h) Examples The rules of this section are illustrated by the following examples:
Example 1. Relating to determination of disqualified persons and nonallocation year if there is no synthetic equity.
(i) Facts. Corporation X is a calendar year S corporation that maintains an ESOP. X has a single class of common stock, of which there are a total of 1,200 shares outstanding. X has no synthetic equity. In 2006, individual A, who is not an employee of X (and is not related to any employee of X), owns 100 shares directly, individual B owns 100 shares directly, and the remaining 1,000 shares are owned by an ESOP maintained by X for its employees. The ESOP's 1,000 shares are allocated to the accounts of individuals who are employees of X (none of whom are related), as set forth in columns 1 and 2 in the following table:
| 1Shareholders | 2Deemed-owned ESOP shares(total of 1,000) | 3Percentage deemed-ownedESOP shares | 4Disqualifiedperson |
|---|---|---|---|
| B | 330 | 33 | Yes. |
| C | 145 | 14.5 | Yes. |
| D | 75 | 7.5 | No. |
| E | 30 | 3 | No. |
| F | 20 | 2 | No. |
| Other participants | 400 (none exceed 10 shares) | 1 or less | No. |
(ii) Conclusion with respect to disqualified persons. As shown in column 4 in the table above, individuals B and C are disqualified persons for 2006 under of this section because each owns at least 10% of X's deemed-owned ESOP shares.
(iii) Conclusion with respect to nonallocation year. However, 2006 is not a nonallocation year under section because disqualified persons do not own at least 50% of X's outstanding shares (the 100 shares owned directly by B, B's 330 deemed-owned ESOP shares, plus C's 145 deemed-owned ESOP shares equal only 47.9% of the 1,200 outstanding shares of X).
Example 2. Relating to determination of disqualified persons and nonallocation year if there is synthetic equity.
(i) Facts. The facts are the same as in Example 1, except that, as shown in column 4 of the table in this example 2, individuals E and F have options to acquire 110 and 130 shares, respectively, of the common stock of X from X:
| 1Shareholders | 2Deemed-ownedESOP shares(total of 1,000) | 3Percentage deemed-owned ESOP shares | 4Options(240) | 5Shareholder percentage of deemed-owned ESOP plus synthetic equity shares | 6Disqualifiedperson |
|---|---|---|---|---|---|
| B | 330 | 33 | Yes (col. 3). | ||
| C | 145 | 14.5 | Yes (col. 3). | ||
| D | 75 | 7.5 | No. | ||
| E | 30 | 3 | 110 | 11.1% ([30 + 91.7] divided by 1,091.7) | Yes (col. 5). |
| F | 20 | 2 | 130 | 11.6% ([20 + 108.3] divided by 1,108.3) | Yes (col. 5). |
| Other participants | 400 (none exceeds 10 shares) | 1 or less | No. |
(ii) Conclusion with respect to disqualified persons. Applying the rule of of this section, E's option to acquire 110 shares of the S corporation converts into 91.7 shares of synthetic equity (110 times the ratio of the 1,000 deemed-owned ESOP shares to the sum of the 1,000 deemed-owned ESOP shares plus the 200 shares held outside the ESOP by A and B). Similarly, F's option to acquire 130 shares of the S corporation converts into 108.3 shares of synthetic equity (130 times the ratio of the 1,000 deemed-owned ESOP shares to the sum of the 1,000 deemed-owned ESOP shares plus the 200 shares held outside the ESOP by A and B). Accordingly, as shown in column 6 in the table above, individual E's synthetic equity shares are counted in determining whether E is a disqualified person for 2006, and individual F's synthetic equity shares are counted in determining whether F is a disqualified person for 2006, but the synthetic equity shares owned by any person do not affect the calculation for any other person's ownership of shares. Accordingly, individuals B, C, E, and F are disqualified persons for 2006.
(iii) Conclusion with respect to nonallocation year. The 100 shares owned directly by B, B's 330 deemed-owned ESOP shares, C's 145 deemed-owned ESOP shares, E's 30 deemed-owned ESOP shares, E's 91.7 synthetic equity shares, F's 20 deemed-owned ESOP shares, plus F's 108.3 synthetic equity shares total 825, which equals 58.9% of 1,400, which is the sum of the 1,200 outstanding shares of X and the 200 shares of synthetic equity shares of X held by disqualified persons. Thus, 2006 is a nonallocation year for X's ESOP under section because disqualified persons own at least 50% of the total shares of outstanding stock of X and the total synthetic equity shares of X held by disqualified persons. In addition, independent of the preceding conclusion, 2006 would be a nonallocation year because disqualified persons own at least 50% of X's outstanding shares because the 100 shares owned directly by B, B's 330 deemed-owned ESOP shares, C's 145 deemed-owned ESOP shares, E's 30 deemed-owned ESOP shares, plus F's 20 deemed-owned ESOP shares equal 52.1% of the 1,200 outstanding shares of X.
Example 3. Relating to determination of number of shares of synthetic equity.
(i) Facts. Corporation Y is a calendar year S corporation that maintains an ESOP. Y has a single class of common stock, of which there are a total of 1,000 shares outstanding, all of which are owned by the ESOP. Y has no synthetic equity, except for four grants of nonqualified deferred compensation that are made to an individual during the period from 2005 through 2011, as set forth in column 2 in the following table, and the ESOP uses the special rules in of this section to determine the number of shares of synthetic equity owned by that individual, as shown in columns 4 and 5:
| 1Determination date | 2Present value of nonqualified deferred compenstion on determination date | 3Share value ondetermination date | 4New shares of syntheticequity ondetermination date | 5Aggregate number of syntheticequity shares on determination date |
|---|---|---|---|---|
| January 1, 2005 | A grant is made on January 1, 2005 with a present value of $1,000. An additional grant of nonqualified deferred compensation with a present value of $775 is made on March 1, 2005 | $10 per share | 100 | 100 |
| January 1, 2006 | An additional grant is made on December 31, 2005 which has a present value of $800 on January 1, 2006. The March 1, 2005 grant has a present value on January 1, 2006 of $800 | $8 per share | 200 | 300 |
| January 1, 2007 | No new grants made | $12 per share | 300 | |
| January 1, 2008 | An additional grant is made on December 31, 2007 which has a present value of $3,000 on January 1, 2008. The grants made during 2005 through 2007 have an aggregate present value on January 1, 2008 of $3,750 | $15 per share | 200 | 450 |
| January 1, 2009 | No new grants are made | $11 per share | 450 | |
| January 1, 2010 | No new grants are made | $22 per share | 450 | |
| January 1, 2011 | No new grants are made. The grants made during 2005 through 2008 have an aggregate present value on January 1, 2011 of $7,600 | $20 per share | 380 |
(ii) Conclusion. The grant made on January 1, 2005, is treated as 100 shares until the determination date in 2008. The grant made on March 1, 2005, is not taken into account until the 2006 determination date and its present value on that date, along with the then present value of the grant made on the preceding day, is treated as a number of shares that are based on the $8 per share value on the 2006 determination date, with the resulting number of shares continuing to apply until the determination date in 2008. On the January 1, 2008, determination date, the grant made on the preceding day is taken into account at its present value of $3,000 on January 1, 2008 and the $15 per share value on that date with the resulting number of shares (200) continuing to apply until the next determination date. In addition, on the January 1, 2008, determination date, the number of shares determined under other grants made between January 1, 2005 and December 31, 2007, must be revalued. Accordingly, the aggregate value of all nonqualified deferred compensation granted during that period is determined to be $3750 on January 1, 2008, and the corresponding number of shares of synthetic equity based on the $15 per share value is determined to be 250 shares on the 2008 determination date, with the resulting aggregate number of shares (450) continuing to apply until the determination date in 2011. On the January 1, 2011, determination date, the aggregate value of all nonqualified deferred compensation is determined to be $7,600 and the corresponding number of shares of synthetic equity based on the $20 per share value on the 2011 determination date is determined to be 380 shares (with the resulting number of shares continuing to apply until the determination date in 2014, assuming no further grants are made).
(i) Effective dates
(1) Statutory effective date
(i) Except as otherwise provided in of this section, section applies for plan years ending after March 14, 2001.
(ii) If an ESOP holding stock in an S corporation was established on or before March 14, 2001, and the election under section with respect to that S corporation was in effect on March 14, 2001, section applies for plan years beginning on or after January 1, 2005.
(2) Regulation effective date
(i) General effective date Except as otherwise provided in of this section, this section applies for plan years beginning on or after January 1, 2005.
(ii) Rules for plan years beginning before January 1, 2005
(A) Except as provided in this , as in effect prior to December 17, 2004 (see § in 26 CFR part 1 revised as of April 1, 2004) applies for plan years ending after October 20, 2003, and beginning before January 1, 2005.
(B) and of this section apply for plan years ending on or after December 31, 2004, but do not apply with respect to an interest held in a qualified subchapter S subsidiary (QSUB) of an S corporation or another entity to which of this section applies before March 15, 2004 if:
(1) All interests in the entity held by individuals who would be disqualified persons under of this section or under guidance issued by the Commissioner before March 15, 2004 are distributed to those individuals as compensation on or before March 15, 2004; and
(2) No such individual has been a participant in the ESOP of the S corporation at any time after October 20, 2003 and before March 15, 2004.
(C) of this section (providing that synthetic equity does not include certain preexisting nonqualified deferred compensation) applies for plan years ending before January 1, 2005.
(D) of this section (permitting an adjustment of the number of synthetic equity shares where an ESOP owns less than 100% of an S corporation) applies for plan years ending before January 1, 2005.
(E) In no event does this apply for any plan year ending before January 1, 2005, for an ESOP holding stock in an S corporation that was established on or before March 14, 2001, if the election under section with respect to that S Corporation was in effect on March 14, 2001.
(iii) Transition rules
(A) Assets held in the account of a disqualified person as of the last day of the first plan year beginning before January 1, 2005, will not be treated as an impermissible accrual with respect to that disqualified person under of this section for the first plan year beginning on or after January 1, 2005, to the extent those assets are not held in that person's account on or after July 1, 2005. Thus, for example, to the extent the assets allocated to the account of a disqualified person as of the last day of the first plan year beginning before January 1, 2005, are transferred to a non-ESOP portion of the plan as described in of this section before July 1, 2005, those assets will not be treated as an impermissible accrual under of this section for the period from the first day of the first plan year beginning on or after January 1, 2005 through June 30, 2005. However, see section , (a)(4), and (e)(2)(C) for excise tax provisions that apply to all deemed-owned shares during the first nonallocation year for the ESOP.
(B) An individual is not treated as a disqualified person during the period from the first day of the first plan year beginning on or after January 1, 2005 through June 30, 2005 if that person would not be a disqualified person during that period under the modified rules of this as of any date during that same period. Further, solely for the purpose of determining whether the first plan year beginning on or after January 1, 2005 is a nonallocation year under section and this section, if that plan year would not have been a nonallocation year under the modified rules of this , then synthetic equity that is not owned by a person on July 1, 2005 is disregarded during the period from the first day of the first plan year beginning on or after January 1, 2005 through June 30, 2005. For purposes of this , the modified rules of this are the rules in as in effect prior to December 17, 2004 (see § in 26 CFR Part 1 revised as of April 1, 2004), modified to exclude from the definition of synthetic equity any stock option, stock appreciation right (payable in cash or stock), or similar rights with respect to shares of the S corporation or a related entity where the facts and circumstances indicate that there is no reasonable likelihood that the holder of the right will receive the shares (or equivalent value). For this purpose, there is no reasonable likelihood that the holder of the right will receive the shares (or equivalent value) in any case in which the option is based on an exercise price that is more than 200% of the fair market value of the shares on the date of grant or the right (in the case of a stock appreciation right or similar right to acquire shares of the S corporation or a related entity) is payable only if the appreciation exceeds 100% of the fair market value of the shares on the date of grant.
(C) For the period from the first day of the first plan year beginning on or after January 1, 2005 through June 30, 2005, there is no nonallocation year under this section if there would be no nonallocation year under this section during that period if this section were applied without regard to of this section (relating to voting rights).
(D) This does not apply to an ESOP for which the first plan year beginning on or after January 1, 2005 begins after June 30, 2005.
[T.D. 9164, 69 FR 75460, Dec. 17, 2004; 70 FR 11121, Mar. 8, 2005]