Reaction of Lithium Acylate α-Carbanions with Carbon Tetrabromide

Abstract

Lithium acylate α-carbanions generated by metalation of acetic, butanoic, and 2-methylpropanoic acids with lithium diisopropylamide in THF under argon reacted with carbon tetrabromide at 20-25°C (2 h) to produce butanedioic acid or its 2,3-diethyl and 2,2,3,3-tetramethyl derivatives, as well as the corresponding 2-bromocarboxylic acids and bromoform. The effect of the halogen nature in carbon tetrahalide (CCl4, CBr4) on the reaction selectivity is discussed.