ATOM TRANSFER ADDITION AND ANNULATION REACTIONS OF PROPARGYL IODOMALONONITRILE

被引：54

作者：

CURRAN, DP

SEONG, CM

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

TETRAHEDRON | 1992年 / 48卷 / 11期

关键词：

IODINE ATOM TRANSFER; RADICAL ADDITION; RADICAL ANNULATION; IODOMALONITRILE;

D O I：

10.1016/S0040-4020(01)88881-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heating of propargyl iodomalononitrile with mono-, di- or trisubstituted alkenes followed by reduction of the crude or isolated products with tributyltin hydride produces dicyano(methylene)cyclopentanes in good to excellent overall yield. This radical annulation is often highly regio and stereoselective. The mechanism is discussed.

引用

页码：2157 / 2174

页数：18

共 41 条

[1]

AYRES RL, 1971, J AM CHEM SOC, V93, P1389

[2] ELECTRONIC AND STERIC EFFECTS IN THE ADDITION OF ELECTROPHILIC 1,3-DICARBONYLALKYL RADICALS TO STYRENES [J].