Fission of Activated Carbon-Nitrogen and Carbon-Sulphur Bonds. X. Polarographic Reduction of Substituted Methyl Phenyl Sulphones

  • O. Manoušek
  • O. Exner
  • P. Zuman

Abstract

Reduction of twenty-six meta- and para-substituted methyl phenyl sulphones at the dropping mercury electrode and at a mercury pool electrode was investigated and by identification of reduction products was decided which of the two functional groupings attached to the benzene ring is reduced. With most derivatives bearing an electron attracting group as a substituent, the methyl sulphonyl group leaves as methane sulphinate anion. A pH-independent, two-electron wave is observed between pH 7 and 14. The reaction represents a kind of aromatic SN2 substitution and is strongly facilitated by conjugation in the transition state with an acceptor group in the para- position. The effect of para-substituents is even greater than expressed by the values of \(\sigma {}_p^ - - x\) substituent constants.

Keywords

Sulphide Benzene Phenyl Recrystallization Nitrite 

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Copyright information

© Plenum Publishing Company Ltd. 1970

Authors and Affiliations

  • O. Manoušek
    • 1
  • O. Exner
    • 1
  • P. Zuman
    • 1
  1. 1.J. Heyrovský Institute of PolarographyCzechoslovak Academy of SciencesPrague 1Czech Republic

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