Reaction of halogens with some α, β-unsaturated aldehydes and ketones

VL Heasley, DF Shellhamer, TL Carter, DE Gipe…

Index: Heasley, Victor L.; Shellhamer, Dale F.; Carter, Tom L.; Gipe, Daphne E.; Gipe, Robert K.; et al. Tetrahedron Letters, 1981 , vol. 22, # 26 p. 2467 - 2470

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Citation Number: 13

Abstract

BrCl addition to methyl acrylate and the methyl crotonates gave both the α-bromo-β-chloro and α-chloro-β-bromo regioisomers, with the latter being the minor product. 1 We anticipated that the carbonyl group in the ketones and aldehydes might accelerate α-attack by chloride in the intermediate halonium ions giving a greater amount of the α-chloro-β-bromo regioisomer. (See reference 1 for a discussion of the effect of carbonyl groups on S N 2 reactions.