Cathodic Cleavage of 1-Trifluoromethyl 1-Alkenyl Sulfone and Sulfoxide

  • Akira Kunugi
  • Md. Abdul Jabbar
  • Hidemitsu Uno
Conference paper


The electrolytic desulfurization of organosulfur compounds has received considerable attention because most of them are valuable synthetic precursors. The previous paper showed that α,β-unsaturated α-fluoro sulfones such as 2-aryl-1-fluorovinyl phenyl sulfones were subjected to cleavage of carbon-sulfur and/or carbon-fluorine bonds to give 2-aryl-1-fluoro-ethylenes and arylethylenes with a molar ratio of about 1:1, in the presence of efficient proton donors such as phenol, acetic acid, and benzoic acid [1]. On the other hand, the electrolytic reduction of α,β-unsaturated α-fluoro sulfoxide such as 2-(4-biphenylyl)-1-fluorovinyl phenyl sulfoxide involves desulfinylation, defluorination followed by reduction of the sulfinyl group, and reduction to the corresponding sulfide, resulting in the formation of 2-(4-biphenylyl)-1-fluoroethylene, 2-(4-biphenylyl)vinyl phenyl sulfide, and 2-(4-biphenylyl)-1-fluorovinyl phenyl sulfide, respectively [2].


Benzoic Acid Acetic Anhydride Organosulfur Compound Single Electron Transfer Electrolytic Reduction 
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References and notes

  1. 1).
    A. Kunugi, K. Yamane, M. Yasuzawa, H. Matsui, H. Uno, and K. Sakamoto, Electrochim. Acta, 38, 1037 (1993).CrossRefGoogle Scholar
  2. 2).
    A. Kunugi, S. Mori, S. Komatsu, H. Matsui, H. Uno, and K. Sakamoto, Electrochim. Acta, 40, 829 (1995).CrossRefGoogle Scholar
  3. 3).
    In the case of 2-(4-biphenylyl)- I-fluorovinyl phenyl sulfoxide, the carboxylated product, 3-(4-biphenylyl)-2-fluoropropenoic acid was produced. See ref 2.Google Scholar

Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Akira Kunugi
    • 1
  • Md. Abdul Jabbar
    • 1
  • Hidemitsu Uno
    • 2
  1. 1.Department of Chemical Science and Technology, Faculty of EngineeringThe University of TokushimaTokushima 770Japan
  2. 2.Advanced Instrumentation Center for Chemical AnalysisEhime UniversityMatsuyama 790Japan

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