REACTION OF PYRROLO[1,2-C]IMIDAZOLE MESOMERIC BETAINES WITH DIPHENYLCYCLOPROPENONE DERIVATIVES

被引：19

作者：

MUSICKI, B ^{[1
]}

机构：

[1] HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 01期

关键词：

D O I：

10.1021/jo00001a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyloaddition reactions of title mesomeric betaines to diphenylcyclopropenone and diphenylcyclopropenethione have been studied. Cycloadditions lead to either 2(1H)-pyridone, 2(1H)-pyridinethione, or bicyclo[3.1.0]hex-3-en-2-one derivatives. Formation of the bicyclo[3.1.0]hex-3-en-2-ones is highly stereoselective with exclusive formation of C-6 exo-alkoxycarbonyl or the exo-acetyl diastereoisomer. Diphenylcyclopropenone and its thione enriched with C-13 at both the 2- and 3-positions were prepared and used to determine the structures of the cycloaddition products. Possible mechanistic pathways for these reactions are considered and compared with previous postulated mechanisms for the cycloadditions of cyclopropenones to N-heterocycles and enamines.

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页码：110 / 118

页数：9

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