Alkali metal reductions of epoxides, ketals, and related heterocycles. Intermediacy of carbanions

EM Kaiser, CG Edmonds, SD Grubb…

Index: Kaiser,E.M. et al. Journal of Organic Chemistry, 1971 , vol. 36, # 2 p. 330 - 335

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Citation Number: 23

Abstract

Solutions of alkali metals in liquid ammonia reduce aromatic epoxides from the" most hindered" position to afford isomerically pure alcohols. Such reductions proceed via the most stable of two possible carbanions as demonstrated by alkylation and deuteration experiments. Aliphatic epoxides are likewise reduced to alcohols. Similar cleavages of aromatic, but not aliphatic, ketals and thioketals afford the corresponding hydrocarbons in ...