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用1,2-二取代乙烯探究过氧碳鎓[3+2]环加成反应:结果与见解

Probing the Peroxycarbenium [3+2] Cycloaddition Reactions with 1,2-Disubstituted Ethylenes: Results and Insights.

作者信息

Xu Ze-Jun, Wittlin Sergio, Wu Yikang

机构信息

State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.

Swiss Tropic and Public Health Institute, Socinstrasse 57, 4002, Basel, Switzerland.

出版信息

Chemistry. 2017 Feb 10;23(9):2031-2034. doi: 10.1002/chem.201605871. Epub 2017 Jan 20.

DOI:10.1002/chem.201605871
PMID:28012253
Abstract

The causes for the title reaction to be limited to only the alkenes with an unsubstituted terminal alkenic carbon were explored. In some "failed" cases the cycloaddition products actually formed but rearranged concurrently. An oxygen atom or a N-Boc (Boc=tert-butyloxycarbonyl) group at the double bond was proven essential for acquisition of intact [3+2] cycloaddition products from 1,2-disubstituted ethylenes.

摘要

我们探究了使该反应仅局限于具有未取代末端烯碳的烯烃的原因。在一些“失败”的案例中,实际上形成了环加成产物,但同时发生了重排。已证明双键处的氧原子或N - 叔丁氧羰基(Boc = 叔丁氧基羰基)基团对于从1,2 - 二取代乙烯获得完整的[3 + 2]环加成产物至关重要。

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