ELECTROCYCLIC AROMATIC-SUBSTITUTION BY NITRILE YLIDES TO GIVE 3H-2-BENZAZEPINES - SUBSTITUENT EFFECTS AND MECHANISM

被引：14

作者：

GROUNDWATER, PW ^{[1
]}

SHARP, JT ^{[1
]}

机构：

[1] UNIV EDINBURGH,DEPT CHEM,W MAINS RD,EDINBURGH EH9 3JJ,MIDLOTHIAN,SCOTLAND

来源：

TETRAHEDRON | 1992年 / 48卷 / 37期

关键词：

ELECTROCYCLIC; NITRILE YLIDE; DIAZO-COMPOUND; BENZAZEPINE;

D O I：

10.1016/S0040-4020(01)80469-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzonitrile 3,3-diarylallyl nitrile ylides (16), generated by the base-induced dehydrochlorination of imidoyl chlorides, cyclised by 1,7-ring closure to give 3H-2-benzazepines e.g. (19), in contrast to analogous diazo-compounds (1) which prefer 1,5-electrocyclisation. Asymmetrically placed substituents [R in (16b-e)] favour substitution at the ortho (2') position irrespective of their polar electronic effects. Deuterium labelling studies have shown that the cyclisation step is irreversible for these nitrite ylides in contrast to the analogous diazo-compounds (3) for which it is reversible.

引用

页码：7951 / 7964

页数：14

共 21 条

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