X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .45. PROTON SPONGE EFFECTS ON THE 1,2-PROTOTROPIC FORMATION OF AZOMETHINE YLIDES FROM ARYLIDENE BENZYLAMINES

被引：14

作者：

GRIGG, R ^{[1
]}

MCMEEKIN, P ^{[1
]}

SRIDHARAN, V ^{[1
]}

机构：

[1] GLAXO RES & DEV,STEVENAGE SG1 2NY,HERTS,ENGLAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 48期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/0040-4020(95)00846-Z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strong rate enhancing effect of an ortho-methoxy or an ortho-dimethylamino group on the 1,2-prototropic generation of azomethine ylides from arylidene arylmethylamines is demonstrated. In the absence of such functionality azomethine ylide formation fails to occur in boiling xylene. The reactions generate the E,E- or syn-azomethine ylide stereoselectively if a single ortho- OMe or -NMe(2) group is present or stereospecifically if either bifurcated H-bonding or push-pull stabilisation of the dipole is possible. Cycloadducts with N-phenylmaleimide are obtained in 78-95% yield.

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收藏

页码：13331 / 13346

页数：16

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