Anodic oxidation of substituted [4-hydroxy-3-coumarinyl]-phenylthiomethanes in acetonitrile. Evidence for a cationic intermediate in carbon-sulfur bond fragmentation

Ibro Tabakovic, Igor Gaon, Mark D. Distefano

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2 Scopus citations

Abstract

The anodic oxidation of substituted [4-hydroxy-3-coumarinyl]-phenylthiomethanes, 1a-1c, in acetonitrile is shown to correspond to a one electron process. The radical cation produced undergoes carbon-sulfur bond fragmentation through loss of a phenylthio radical to give a cation which is trapped by Ritter reaction with acetonitrile to yield the final products 2a-2c in 64-82% yield. In the case of geranyl [4-hydroxy-3-coumarinyl]-phenylthiomethane, Id, the intermediate allylic cation is attacked intramolecularly by a hydroxy nucleophile followed by loss of a proton, to give 2d in 40% yield.

Original languageEnglish (US)
Pages (from-to)1773-1778
Number of pages6
JournalElectrochimica Acta
Volume43
Issue number12-13
DOIs
StatePublished - May 5 1998

Keywords

  • Cyclic voltammetry
  • Geranyl [4-hydroxy-3-coumarinyl]-phenylthiomethane
  • Preparative anodic oxidation
  • Reaction mechanism
  • Substituted [4-hydroxy-3-coumarinyl]-phenylthiomethanes

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