Canadian Journal of Chemistry

The electrophilic addition of dimethylbromosulfonium bromide to conjugated enones: efficient synthesis of α-bromo enones

YL Chow, BH Bakker

Index: Chow, Yuan L.; Bakker, Bert H. Canadian Journal of Chemistry, 1982 , vol. 60, p. 2268 - 2273

Full Text: HTML

Citation Number: 31

Abstract

Dimethylbromosulfonium bromide reacted readily with many enones at 0° C or lower to precipitate a-bromo-β-sulfonium conjugated enones. These salts eliminate a proton and dimethylsulfide readily with aqueous potassium carbonate to give excellent yields of α- bromo conjugated enones cleanly. The mechanism of the addition was explained by the bromonium ion initiated 1, 4-addition followed by tautomerization of enol hypobromites.

Related Articles:

Three bacteriorhodopsins with ring??didemethylated 6??s??locked chromophores and their properties

[Groesbeek, M.; Galen, A. J. J. van; Ippel, J. H.; Berden, J. A.; Lugtenburg, J. Recueil des Travaux Chimiques des Pays-Bas, 1993 , vol. 112, # 4 p. 237 - 246]

The Preparation of α-Bromo-α, β-unsaturated Ketones and Esters

[Nield Journal of the American Chemical Society, 1945 , vol. 67, p. 1146]

More Articles...