SMALL RING SYSTEMS FORM ISOCYANIDES .I. REACTION OF ISOCYANIDES WITH HEXAFLUOROBUTYNE-2

被引：61

作者：

OAKES, TR

DAVID, HG

NAGEL, FJ

机构：

[1] Department of Chemistry, Cleveland State University, Cleveland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1969年 / 91卷 / 17期

关键词：

D O I：

10.1021/ja01045a030

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The use of the characteristic α,α-addition reaction of isocyanides as a method for the formation of a small membered ring system has been investigated. In inert solvents, isocyanides react with 2 mol of hexafluorobutyne-2 to produce cyclopropenylketenimine derivatives. None of the simple 1:1 adducts (the anticipated imino-cyclopenone derivatives) were detected. The cyclopropenylketenimines were easily hydrolyzed to the corresponding cyclopropenylamides and reduced to cyclopropane derivatives. When isocyanides were allowed to react with hexafluorobutyne-2 in ethanol as solvent, two different 1:1:1 adducts (isocyanide: butyne: ethanol) were obtained, a ketenimine and a conjugated imino ester. The structure of these 1:1:1 adducts imply the prior formation of a 1:1 intermediate that may have predominant carbene or carbanion character. © 1969, American Chemical Society. All rights reserved.

引用

页码：4761 / &