Reaction of Lithium Acylate α-Carbanions with Carbon Tetrachloride

Abstract

Metalation of acetic, butanoic, or 2-methylpropanoic acid with lithium diisopropylamide in tetrahydrofuran under argon gave the corresponding lithium acylate α-carbanions which reacted with carbon tetrachloride at 20–25°C for 2 h to afford butanedioic acid or its 2,3-diethyl and 2,2,3,3-tetramethyl derivatives, as well as the corresponding α-chlorocarboxylic acids and chloroform. A radical mechanism was proposed for the formation of dicarboxylic and α-chlorocarboxylic acids.