The Journal of Organic Chemistry

Reactions of haloketenes with allyl ethers and thioethers: a new type of Claisen rearrangement

R Malherbe, G Rist, D Bellus

Index: Malherbe, Roger; Rist, Guenther; Bellus, Daniel Journal of Organic Chemistry, 1983 , vol. 48, # 6 p. 860 - 869

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Citation Number: 65

Abstract

A new reaction of dichloroketene (2) with allylic ethers, sulfides, and selenide 1 has been observed. A [3, 3] sigmatropic rearrangement takes place at room temperature, leading to cu, a'-dichloro-y J-unsaturated esters 3. The scope of this reaction was further investigated with dibromoketene (16), difluoroketene (17), electron-deficient chloroketenes, and different allylic systems. In the course of these studies, total syntheses of two naturally occurring ...