OXIRANE RADICALS . THERMAL DECOMPOSITION OF T-BUTYL CIS- AND TRANS-ALPHA BETA-DIPHENYLPERGLYCIDATES
OXIRANE RADICALS . THERMAL DECOMPOSITION OF T-BUTYL CIS- AND TRANS-ALPHA BETA-DIPHENYLPERGLYCIDATES
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DOI：
10.1021/jo01256a010
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发表时间：
1969-01-01
影响因子：
3.6
通讯作者：
DAS, NC
中科院分区：
文献类型：
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作者：
PADWA, A;DAS, NC
二叔丁基过氧化物引发的2, 3-cts-and-Zraras-二苯基-2, 3-环氧丙烷的脱羰反应以及正丁基顺式和反式-a, 0-二苯基过缩水甘油酯的热分解已作为异构环氧乙烷自由基的来源进行了研究。脱羰反应获得的产物完全源自环氧乙烷环的打开。¿-丁基顺式-和反式-，| S-二苯基高缩水甘油酯在枯烯中以相同的速率在 70 ℃下通过非协同单键裂解进行热分解。由任一过酯形成的产物(脱氧苯偶姻、氧化二苯乙烯和1,2,3,4-四苯基-1,4-丁二酮)是相同的。结果表明，环氧乙烷自由基可以夺取氢，但重排成去磺基自由基很容易，并且占产物的主要比例。
The di-f-butyl peroxide initiated decarbonylation reactions of 2, 3-cts-and-Zraras-diphenyl-2, 3-epoxypropanaI and the thermal decomposition of¿-butyl cis-and trans-a, 0-diphenylperglycidates have been investigated as sources of isomeric oxirane radicals. The products obtained from the decarbonylation reactions are exclusively derived from opening of the oxirane ring.¿-Butyl cis-and trans-,| S-diphenylperglycidates undergo thermal decomposition in cumene at 70 at identical rates and by a nonconcerted one-bond cleavage. The products (desoxybenzoin,¿ rons-stilbene oxide, and l, 2, 3, 4-tetraphenyl-l, 4-butanedione) formed are the same from either perester. The results indicate that the oxirane radical can abstract hydrogen butthat rearrangement to the desyl radical is facile and accounts for the major proportion of products.