Electrocyclic effects in solvolysis. 2. Synthesis and solvolysis of .beta.,.beta.-divinyl-.beta.-phenethyl tosylate
Electrocyclic effects in solvolysis. 2. Synthesis and solvolysis of .beta.,.beta.-divinyl-.beta.-phenethyl tosylate
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溶剂分解中的电循环效应。
DOI：
10.1021/jo01328a044
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发表时间：
1979
影响因子：
3.6
通讯作者：
R. Niinemae
中科院分区：
文献类型：
--
作者：
J. Wilt;R. Niinemae
为了寻求溶剂解过程中芳基迁移与电环闭环的耦合，我们在二恶烷水溶液和乙酸中制备并溶剂化了标题甲苯磺酸酯。通过乙烯基（主要）和苯基（次要）迁移，产物完全重新排列。没有检测到通过所寻求的电环闭合的环化。标题甲苯磺酸酯的乙酰分解速率与新植磺酸酯相当，表明诱导延迟和以乙烯基为中心的嵌合加速的对立因素的平衡。
To seek aryl migration coupled with electrocyclic ringclosure during solvolysis, we prepared and solvolyzed the title tosylate in aqueous dioxane and in acetic acid. The products were completely rearranged, both by vinyl (major) and phenyl (minor) migration. No cyclization via the sought electrocyclic closure was detected. The rate of acetolysis of the title tosylate was comparable to that of neophyltosylate, indicating a balance of the opposing factors of inductive retardation and anchimeric acceleration centered in the vinyl groups.