Reaction of Lithium Acylate α-Carbanions with Carbon Tetrachloride
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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.
Keywordsdicarboxylic acids lithium acylate α-carbanions metalation oxidative coupling electron transfer carbon tetrachloride chlorination α-chlorocarboxylic acids
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