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
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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.
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