Ammonium ylide versus carbonyl ylide formation in the rhodium(II)-catalyzed decomposition of diazoacetylureas. Generation and X-ray structure of a stable five-membered N-acyl ammonium ylide.

被引：9

作者：

Kappe, CO

机构：

[1] Institute of Organic Chemistry, Karl-Franzens-University Graz., A-8010 Graz

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(97)00618-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Rh(II)-catalyzed decomposition of diazoacetylurea 5 gives rise to carbenoid intermediate 7 which can either cyclize to ammonium ylide 6 or to the isomeric carbonyl ylide dipole 8. In the presence of a rhodium catalyst, ammonium ylide 6 rearranges to carbonyl ylide 8 which undergoes 1,3-dipolar cycloaddition reaction with DMAD to give furan 12. (C) 1997 Elsevier Science Ltd.

引用

页码：3323 / 3326

页数：4