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Russian Journal of General Chemistry

, Volume 89, Issue 1, pp 148–150 | Cite as

Reactions of Lithium Acylates α-Carbanions with 1,2-Diiodoethane

  • A. V. Zorin
  • A. R. ChanyshevaEmail author
  • A. O. Lenkova
  • V. V. Zorin
Letters to the Editor
  • 4 Downloads

Abstract

The interaction of lithium acylates α-carbanions (obtained via metallation of acetic, butyric, and isobutyric acids with lithium diisopropylamide) with 1,2-diiodoethane under argon in tetrahydrofuran at 20–25°C has proceeded as oxidative cross-coupling of enolate anions to form succinic, 2,3-diethylsuccinic, and 2,2,3,3-tetramethylsuccinic acids with yields 50, 53, and 16%, respectively. The products of sequential nucleophilic substitution of iodine atoms with alkyloxycarbonyl species have not been detected.

Keywords

1,2-diiodoethane dicarboxylic acids lithium acylates α-carbanions metallation oxidative cross-coupling 

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. V. Zorin
    • 1
  • A. R. Chanysheva
    • 1
    Email author
  • A. O. Lenkova
    • 1
  • V. V. Zorin
    • 1
  1. 1.Ufa State Petroleum Technological UniversityUfaRussia

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