ON THE ORIGIN OF GEMINAL REGIOSELECTIVITY IN THE ENE REACTION OF SINGLET OXYGEN WITH SUBSTITUTED ALKENES

被引：26

作者：

ADAM, W

RICHTER, MJ

机构：

[1] Institute of Organic Chemistry, University of Würzburg, D-97074 Würzburg, Am Hubland

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(00)61349-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The geminal regioselectivity observed in the ene reaction between singlet oxygen and alkenes with anion-stabilizing groups is rationalized on the basis of a perepoxide intermediate, in which in analogy to the nucleophilic attack on protonated epoxides, the perepoxide is opened preferentially at the C-O bond weakened by the substituent.

引用

收藏

页码：8423 / 8426

页数：4

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