METAL-HALOGEN EXCHANGE-INITIATED INTRAMOLECULAR CONJUGATE ADDITION-REACTIONS OF CONJUGATED ACETYLENIC ESTERS

被引：20

作者：

COOKE, MP

机构：

[1] Department of Chemistry, Washington State University, Pullman

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 24期

关键词：

D O I：

10.1021/jo00076a053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lithium-iodine exchange-initiated intramolecular conjugate addition reactions of some model gamma-iodo-alpha,beta-acetylenic esters have been examined. Product mixtures arising from proton abstraction reactions were observed in reactions leading to 5-membered ring formation. More efficient cyclizations resulted when reactions were conducted in the presence of trimethylsilyl chloride to trap intermediate allenolate ions. Allenolate ion trapping by an internal electrophilic center in 26 resulted in the highly efficient formation of bicyclic ester 27.

引用

页码：6833 / 6837

页数：5

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