1-Phenylcyclohexene from trans-2-Phenylcyclohexyltrimethylammonium Hydroxide by cis Elimination1
1-Phenylcyclohexene from trans-2-Phenylcyclohexyltrimethylammonium Hydroxide by cis Elimination1
复制标题
通过顺式消除从反式-2-苯基环己基三甲基氢氧化铵中生成 1-苯基环己烯1
DOI：
10.1021/ja01479a028
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发表时间：
1961
影响因子：
15
通讯作者：
D. L. Ross
中科院分区：
文献类型：
--
作者：
A. C. Cope;G. A. Berchtold;D. L. Ross
< raĞs-]-Dimethylamino-2-phenylcyclohexane-3 3, 6, 6-< Z4 has been synthesized from butadiene-1, 1, 4, 4-di, obtained from the base-catalyzed equilibration with deuterium oxide and subsequent pyrolysis of 2, 5-dihydrothiophene-l, 1-dioxide (buta-diene sulfone). Thequaternary base derived from this amine decomposed thermally forming 1-phenylcyclohexene without loss of deuterium, proving that this Hofmann elimination is a cis elimination in which only the 0-hydrogen atom in the 2 (benzyl)-position is lost.The thermal degradation of íraras-2-phenyl-cyclohexyltrimethylammonium hydroxide has been reported to give pure 1-phenylcyclohexene. 3 It was suggested that 3-phenylcyclohexene is first formed by a normal trans elimination and that this product then undergoes a base-catalyzed prototropic shift to the more stable conjugated system. Examples of such a rearrangement which had been observed previously are the formation of 1, 3-pentadiene in the exhaustive methylation of piperidine4 and the isolation of propenylbenzene from the exhaustive methylation of 3-phenylpro-
