Corporate & Partner Tax Instructor: Dwight Drake Two Liquidation Modes Corp Shareholders Corp Corporate Assets Stock Cancelled Straight Liquidation Mode Third Party Corporate Assets Cash, Notes Cash, Notes Stock Cancelled Sale and Liquidation Mode

Corporate & Partner Tax Instructor: Dwight Drake Complete Liquidation – Shareholder Impact General Rule: Per 331, complete liquidation treated as sale or exchange of stock, producing capital gain or loss equal to difference between cash and FMV of property received and shareholder’s basis in stock. Section 301 not apply. Timing Issues: - When did liquidation began and dividends (non-liquidating) distributions end. Fact question. Look to corporate resolutions and adoption of plan installment sales treatment applies when liquidating distributions over time. Open transaction treatment very risky; appears trumped by installment treatment permitted even as to installment obligations acquired by non-public corp in asset sell-off and distributed to shareholders. To qualify under 453, corp sale that created obligation must be with 12 month period after liquidation plan adopted and liquidation must be completed within same period. Inventory and “dealer” qualify only if part of bulk sale of assets.

Corporate & Partner Tax Instructor: Dwight Drake Complete Liquidation – Corporation Impact General Rule: Per 336, Corp recognizes gain or loss on property distributed or sold as part of complete liquidation. 267 related-party loss limitations not apply in complete liquidation. (d)(1) Related Party Exception: No loss at all on distribution to related party (per 267) in complete liquidation if: - Distribution not pro rata, or - Distributed property acquired by corp in 351 transaction or as contribution to capital within 5 yrs of distribution (“Disqualified Property”). (d)(2) Tax Avoidance Exception: No built-in loss (loss at time of acquisition) allowed if property acquired in 351 transaction or contribution to capital and principal purpose was to recognize loss on liquidation. If acquired within 2 yrs of plan of liquidation, bad purpose a done deal unless there is “clear and substantial relationship” between property and conduct of business and solid explanation. If outside 2yr window, probably safe except in “most rare” cases.

Corporate & Partner Tax Instructor: Dwight Drake Problem 661 Basic Facts: A owns 100 shares of H Corp, cost 10k. H Corp E&P – 12k. H Corp liquidates. (a)A gets 20k cash in liquidation. A has LTCG of 10k per 331(a). (b)A gets 10k yr 1 and 10k yr 2. Under 453, A recognizes 5k LTCG in year 1 and 5k LTCG in year 2. Service allows open reporting if amount uncertain; if so, no gain until basis recovered. Can elect to opt out of 453; then full 10k LTCG in year 1. If no plan a liquidation in year 1, may be issue of whether both distributions are part of liquidation (fact issue). If not, then year 1 distribution 10k ordinary income dividend under 301; yr 2 liquidating distribution and no gain.

Corporate & Partner Tax Instructor: Dwight Drake Problem 661 Basic Facts: A owns 100 shares of h Corp, cost 10k. H Corp E&P – 12k. H Corp liquidates. (c)A gets in liquidation 8k cash and 12k note, payable 1k per yr for 12 yrs. H obtained note on sale of capital asset as part of liquidation. A realizes 10k LTCG on sale. Per 453(h), installment reporting available on note if obtained by corp within 12 month period after adoption of plan of liquidation and liquidation completed in 12 months after plan. Gross profit percentage is 50%. Hence, 4k LTCG yr 1 on receipt of 8k and.5k in each following year on receipt of 1k. If H stock publicly traded, 453(k)(2)(A) precludes use of k LTCG. (d)Same as (d), but installment obligation received by H two yrs ago and no payments made. No hope for installment reporting because obtained before plan of liquidation. 10K LTCG in year 1 and basis in note 12k. (e)After liquidation, A pays 5k judgment against old H. Per Arrowsmith case, this 5k LTCL to A even though would have been deductible to H Corp. Character of loss determined with reference to LTCG reported by A.

Corporate & Partner Tax Instructor: Dwight Drake Problem 674 Basic Facts: X Corp stock owned by I (60) shares and F (40 shares). No liabilities and following assets. On 1/1, adopts plan of liquidation. Basis FMV Gainacre 100k 400k Lossacre 800k 400k Cash 200k 200k (a)All assets distributed to I and F pro-rata as tenants-in-common. X Corp has 300k gain on Gainacre and 400k loss on Lossacre. Shareholders take basis equal to FMV per 334(a). 336(d) loss limitation not apply because distribution pro rata and assets held over 5 yrs. (b)I gets Lossacre and cash; F gets Gainacre. X has 300k gain on Gainacre. Loss on Loassacre not allowed per 336(d)(1) because I is related person per 267 (more than 50%) and distribution not pro rata. I’s basis in Lossacre still 400k; loss in permanently gone.

Corporate & Partner Tax Instructor: Dwight Drake Problem 674 Basic Facts: X Corp stock owned by I (60) shares and F (40 shares). No liabilities and following assets. On 1/1, adopts plan of liquidation. Basis FMV Gainacre 100k 400k Lossacre 800k 400k Cash 200k 200k (c)X distributes Gainacre and 200k to I and Lossacre to F. X recognizes 300k on Gainacre and 400k loss on Lossacre. Although not pro rata, F not related person under 267 because not over 50% owner. Thus, 336(d) limit not apply. (d) Same pro rata as (a), but X acquired Lossacre 4 yrs ago as contribution to capital. Still 300k gain on Gainacre. 60% portion to Lossacre loss (240k) not allowed per 336(d) because go to I and “disqualified property” because acquired within 5 yrs or 351 transaction. Loss on portion to F (160k) allowed. I and F still take basis equal to FMV. Same result if Lossacre has 1 mill FMV and 800k basis on contribution to capital. For 336(d)(1) purposes, built-in gain or loss not applicable.

Corporate & Partner Tax Instructor: Dwight Drake Problem 674 Basic Facts: X Corp stock owned by I (60) shares and F (40 shares). No liabilities and following assets. On 1/1, adopts plan of liquidation. Basis FMV Gainacre 100k 400k Lossacre 800k 400k Cash 200k 200k (e)Gainacre and cash to I; Lossacre to F; Lossacre have no relationship to X business and acquired by 351 transfer from I and F 18 months prior to plan of liquidation when FMV 700k and basis 800k. 336(b)(1) disallowance not apply because F not 267 related party. But 336(b)(2) anti-stuffing rule might apply because 351 transaction within 2 yrs of plan. If 362(e)(2) basis adjustment made at contribution, no need for 336(b)(2) anti-stuffing – loss never realized. If no 336(e)(2) adjustment, then 100k pre-contribution loss disallowed per 336(b)(2), but 300k post-contribution loss allowed. No hope of rebutting 2 yr taint presumption because asset not related to X business.

Corporate & Partner Tax Instructor: Dwight Drake Problem 674 Basic Facts: X Corp stock owned by I (60) shares and F (40 shares). No liabilities and following assets. On 1/1, adopts plan of liquidation. Basis FMV Gainacre 100k 400k Lossacre 800k 400k Cash 200k 200k (f) I and F own X Corp I contributed Gainacre and Lossacre; F contributed cash in 351 deal. Lossacre is 336(d)(1) “disqualified property”, 362(e)(2) applied at contribution, 336(d)(2) not apply because no “plan” for X to recognize loss on liquidation. X distributes each asset pro-rata to parties in liquidation (e)(2) basis reduction is 100k (900k less 800k) based on I’s contibution of assets. - Of remaining 300k built-in loss on Lossacre, 80% (240k) disallowed because I related party. Remaining 20% (60k) allowed as loss to X.

Corporate & Partner Tax Instructor: Dwight Drake Problem 674 Basic Facts: X Corp stock owned by I (60) shares and F (40 shares). No liabilities and following assets. On 1/1, adopts plan of liquidation. Basis FMV Gainacre 100k 400k Lossacre 800k 400k Cash 200k 200k (g) Same as (f), but there was plan to have X recognize built-in loss. Then entire built-in loss disallowed per 336(d)(2). Fact that portion of Lossacre went to F (20% shareholder) irrelevant.