The Mechanism of the C-S Bond Cleavage in Electron Transfer Reactions of α-Organothio-Substituted Heteroatom Compounds

  • Jun-ichi Yoshida
  • Masanobu Sugawara
  • Masayuki Imagawa
Conference paper


Electron transfer reactions of α-organothio-substituted heteroatom compounds lead to the cleavage of the C-S bond and the introduction of nucleophiles to the carbon. For example, It has been reported that the oxidation of α-organothio ethers in acetic acid results in the cleavage of the carbon-sulfur bond and the introduction of the acetoxyl group onto the carbon.1 The anodic oxidation of aorganothio ethers in methanol also gives the dimethyl acetal.2 In the anodic oxidation of benzyl sulfides, the C-S bond is cleaved and a nucleophile is introduced onto the carbon.3 Photoelectron transfer is also effective to cleave the carbon-sulfur bond.4


Bond Cleavage Cation Radical Anodic Oxidation Electron Transfer Reaction Molecular Orbital Calculation 
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Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Jun-ichi Yoshida
    • 1
  • Masanobu Sugawara
    • 1
  • Masayuki Imagawa
    • 1
  1. 1.Department of Synthetic Chemistry & Biological Chemistry Graduate School of EngineeringKyoto UniversityKyotoJapan

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