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Russian Chemical Bulletin

, Volume 42, Issue 1, pp 129–131 | Cite as

Possibility of applying the electrochemical version of the Horner reaction to the synthesis of unsaturated lactones

  • V. A. Petrosyan
  • L. V. Adaevskaya
  • O. S. Chizhov
  • A. Yu. Romanovich
Organic Chemistry

Abstract

Direct electrochemical reduction of specially synthesized 2-[(diethoxyphosphorylacetoxy] benzaldehyde on a platinum electrode in an aprotic medium is accompanied by ester bond cleavage, and not formation of coumarin via the phosphonate-anion followed by intramolecular Horner cyclization. This could be realized, as a matter of principle, in the presence of an ionol anion (2,6-di-tert-butyl-4-methylphenoxide), electrochemically generatedin situ.

Key words

Wittig-Horner reaction unsaturated lactones synthesis intramolecular cathode cyclization electrochemically generated base coumarin 2,6-di-tert-butyl-4-methyl-phenoxide 

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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • V. A. Petrosyan
    • 1
  • L. V. Adaevskaya
    • 1
  • O. S. Chizhov
    • 1
  • A. Yu. Romanovich
    • 1
  1. 1.N.D.Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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