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Russian Journal of Organic Chemistry

, Volume 55, Issue 1, pp 42–46 | Cite as

Reaction of Lithium Acylate α-Carbanions with Carbon Tetrachloride

  • A. V. ZorinEmail author
  • A. T. Zaynashev
  • V. V. Zorin
Article
  • 2 Downloads

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.

Keywords

dicarboxylic acids lithium acylate α-carbanions metalation oxidative coupling electron transfer carbon tetrachloride chlorination α-chlorocarboxylic acids 

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  1. 1.Ufa State Petroleum Technological UniversityUfa, BashkortostanRussia

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