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Chemistry of Heterocyclic Compounds

, Volume 29, Issue 8, pp 909–917 | Cite as

Electrochemical reduction of 1-sulfonylbenz[c,d]indolin-2-ones, and the structure of the free radicals that are formed

  • Ya. Stradyn'
  • L. Baumane
  • R. Gavars
  • V. I. Magda
  • Yu. V. Samusenko
Article
  • 39 Downloads

Abstract

In the electrochemical reduction of N-sulfonylbenz[c,d]indolin-2-ones, anion radicals that are detectable by ESR may be formed, with structures that correspond to either the original molecule or isomers of that molecule. Substituents that localize the unpaired electron density on the naphthalene ring system increase the probability of forming ESR-detectable free radicals. In the primary anion radicals, the unpaired electron is localized mainly (>70%) on the naphthalene nucleus. Replacement of the keto group in the molecules of naphthostyrils by a thiocarbonyl group increases the unpaired electron density on the naphthalene ring system of the primary anion radicals. For all of the compounds, parameters of electrochemical reduction in dimethylformamide have been established, under conditions of polarography and cyclic voltammetry.

Keywords

Organic Chemistry Free Radical Naphthalene Cyclic Voltammetry Anion Radical 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • Ya. Stradyn'
    • 1
    • 2
  • L. Baumane
    • 1
    • 2
  • R. Gavars
    • 1
    • 2
  • V. I. Magda
    • 1
    • 2
  • Yu. V. Samusenko
    • 1
    • 2
  1. 1.Latvian Institute of Organic SynthesisRiga
  2. 2.Poltava Pedagogical InstitutePoltava

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