Base-catalyzed transformation of a β-dicarbonyl acetal, 1-(2-hydroxyphenyl)-2-phenyl-3,3-dimethoxypropane-1-one into isoflavone and 2-hydroxydeoxybenzoin

M. Zsuga, V. Szabó, L. Balogh

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Abstract

The reactions of base sensitive acetal X under alkaline conditions were studied. The decomposition of X depends on the OH- concentration. At low [OH-]≦10-3 M, X transforms into I, while at [OH-]=10-2 M, it decomposes to V via an enol-enolate equilibrium (IV⇌VI). These unusual base-catalyzed transformations are explained by the high mobility of the α-proton of X, and by the stability of I towards nucleophilic reagents.

Original languageEnglish
Pages (from-to)1-6
Number of pages6
JournalReaction Kinetics and Catalysis Letters
Volume8
Issue number1
DOIs
Publication statusPublished - Mar 1 1978

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

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