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.
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页码：3323 / 3326
页数：4
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