The vicarious nucleophilic substitution of hydrogen proceeding via a cyclopropane ring-opening

被引：3

作者：

Stalewski, J ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 51期

关键词：

cyclopropanes; carbanions; nitro compounds; substitution;

D O I：

10.1016/S0040-4039(98)02114-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Cyano-2,2-diethoxycarbonyl cyclopropane was reacted with several nitroarenes under basic conditions. The reaction proceeded according to the vicarious nucleophilic substitution of hydrogen scheme; i.e. the initially formed sigma-adducts underwent base-induced elimination, resulting in cleavage of the cyclopropane ring. The ortho-substituted products can be directly transformed into substituted N-hydroxyindoles. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9523 / 9526

页数：4

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