The Journal of organic chemistry

Novel preparation of α, β-unsaturated aldehydes. Benzeneselenolate promotes elimination of HBr from α-bromoacetals

A Vasil'ev, L Engman

Index: Vasil'ev, Andrei; Engman, Lars Journal of Organic Chemistry, 2000 , vol. 65, # 7 p. 2151 - 2162

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Citation Number: 14

Abstract

Acetalization, α-bromination, nucleophilic phenylselenenylation, oxidative elimination/hydrolysis was investigated as a novel protocol for the α, β-dehydrogenation of aldehydes. Treatment of acetals with bromine in methylene chloride afforded the corresponding α-bromoacetals in 80-90% yields. Nucleophilic phenylselenenylation was then conveniently effected by treatment with benzeneselenolate generated in situ in ...