Tetrahedron

Allene epoxidation: synthesis of functionalized lactones by the DMDO oxidation of allenic acids

JK Crandall, E Rambo

Index: Crandall, Jack K; Rambo, Elisa Tetrahedron, 2002 , vol. 58, # 35 p. 7027 - 7036

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Citation Number: 30

Abstract

A series of allenic carboxylic acids has been converted to functionalized lactones by oxidation–cyclization promoted by dimethyldioxirane. These transformations are rationalized by the involvement of unisolated allene oxide and spirodioxide intermediates. The structures of the starting allenic acids and the reaction conditions determine which of these two intermediate species serves as the source of the isolated products. The use of prepared ...