Electrochemical transformation of malononitrile and carbonyl compounds into functionally substituted cyclopropanes: Electrocatalytic variant of the wideqvist reaction

被引：79

作者：

Elinson, MN ^{[1
]}

Feducovich, SK ^{[1
]}

Lizunova, TL ^{[1
]}

Nikishin, GI ^{[1
]}

机构：

[1] ND Zelinskii Organ Chem Inst, Moscow 117913, Russia

来源：

TETRAHEDRON | 2000年 / 56卷 / 19期

基金：

俄罗斯基础研究基金会;

关键词：

electrochemical reaction; catalysis; cyclopropanes; ketones;

D O I：

10.1016/S0040-4020(00)00195-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Electrolysis of malononitrile and carbonyl compounds in the presence of alkali metal halides in an undivided cell results in the formation of substituted 1,1,2,2-tetracyanocyclopropanes in 60-90% yield. This electrocatalytic variant of the Wideqvist reaction using malononitrile instead of bromomalonitrile was successfully performed. Electrocatalytic transformation of substituted 1,1,2,2-tetracyanocyclopropanes in methanol or ethanol in an undivided cell leads to substituted 2-amino-4,4-dialkoxy-1,5-dicyano-3-azabicyclo[3.1.0]hex-2- enes in 70-95% yields after 0.05-0.10 F/mol of electricity has been passed. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3063 / 3069

页数：7

共 21 条

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ISOINDOLENINES AS INTERMEDIATE PRODUCTS OF THE PHTHALOCYANIN SYNTHESIS [J].