Organic letters

Preparation of α-haloacrylate derivatives via dimethyl sulfoxide-mediated selective dehydrohalogenation

W Li, J Li, ZK Wan, J Wu, W Massefski

Index: Li, Wei; Li, Jianchang; Wan, Zhao-Kui; Wu, Junjun; Massefski, Walter Organic Letters, 2007 , vol. 9, # 22 p. 4607 - 4610

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Citation Number: 31

Abstract

Dimethyl sulfoxide causes α, β-dihalopropanoate derivatives to undergo efficient, selective dehydrohalogenation to form α-haloacrylate analogues. A variety of α-halo Michael acceptors were prepared in dimethyl sulfoxide under mild, base-free conditions, including the preparation of α-bromoacrolein and α-chloro-and bromoacrylonitriles. Synthesis of these molecules has been reported in the literature to be difficult. Among all the existing ...