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Reaction of Lithium Acylate α-Carbanions with Carbon Tetrachloride

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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.

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Authors and Affiliations

  1. Ufa State Petroleum Technological University, ul. Kosmonavtov 1, 450062, Ufa, Bashkortostan, Russia

    A. V. Zorin, A. T. Zaynashev & V. V. Zorin

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  1. A. V. Zorin
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  2. A. T. Zaynashev
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  3. V. V. Zorin
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Correspondence to A. V. Zorin.

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Zorin, A.V., Zaynashev, A.T. & Zorin, V.V. Reaction of Lithium Acylate α-Carbanions with Carbon Tetrachloride. Russ J Org Chem 55, 42–46 (2019). https://doi.org/10.1134/S1070428019010068

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  • DOI: https://doi.org/10.1134/S1070428019010068

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