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Reactions of Tricyclo[4.1.0.0 2,7 ]heptane and 1-Methyltricyclo[4.1.0.0 2,7 ]heptane with 2-Bromoethanesulfonyl Bromide
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2020-07-20 , DOI: 10.1134/s1070428020060081
S. G. Kostryukov , Yu. Yu. Masterova

Abstract

2-Bromoethanesulfonyl bromide reacts with tricyclo[4.1.0.02,7]heptane and 1-methyltricyclo[4.1.0.02,7]heptane according to a radical mechanism to give products of both anti and syn addition across the C1–C7 central bicyclobutane bond having a norpinane (bicyclo[3.1.1]heptane) structure. Treatment of the adducts with triethylamine leads to the formation of vinyl sulfones as a result of 1,2-dehydrobromination, and their reaction with sodium methoxide involves 1,2- and 1,3-dehydrobromination and nucleophilic addition, depending on the substrate structure and reactant ratio.


中文翻译:

三环[4.1.0.0 2,7]庚烷和1-甲基三环[4.1.0.0 2,7]庚烷与2-溴乙烷磺酰基溴的反应

摘要

用三环2- Bromoethanesulfonyl溴化物进行反应[4.1.0.0 2,7 ]庚烷和1- methyltricyclo [4.1.0.0 2,7 ]庚烷根据游离基机理,得到两者的产品合成加法工作在C 1 -C 7具有正庚烷(双环[3.1.1]庚烷)结构的中心双环丁烷键。用三乙胺处理加合物会导致1,2-脱氢溴化反应生成乙烯基砜,取决于底物的结构和结构,它们与甲醇钠的反应涉及1,2-和1,3-脱氢溴化反应以及亲核加成反应。反应物比率。
更新日期:2020-07-20
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