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Electrogenerated cation radicals of heteroaromatic N-oxides and oxidation of cyclohexane induced by them

  • Physical Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

The primary products of electrooxidation of heteroaromatic N-oxides are the corresponding cation-radicals. The redox properties of N-oxides, and also the stability of the cation-radicals generated from them, are determined by the number of N atoms and N-oxide groups in the heterocyclic ring and also by the nature of the substituents. Using phenazine di-N-oxide as an example, it was shown that the generation of the cation radical induces the oxidation of cyclohexane into cyclohexanol and cyclohexanone and is accompanied by deoxygenation of the di-N-oxide into a mono-N-oxide. The oxidation of cyclohexane proceeds by two paths, in one of which molecular oxygen participates, while in the second path an oxygen transfer probably takes place from the di-N-oxide cation radical to cyclohexane.

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Authors and Affiliations

  1. Institute of Chemical Physics, Academy of Sciences of the USSR, Chernogolovka Branch, USSR

    E. M. Koldasheva, Yu. V. Geletii, V. V. Yanilkin & V. V. Strelets

Authors
  1. E. M. Koldasheva
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  2. Yu. V. Geletii
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  3. V. V. Yanilkin
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  4. V. V. Strelets
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 994–999, May, 1990.

The authors wish to express their gratitude to A. E. Shilov for his participation in the discussion of the results, and also to R. E. Lokhov and A. V. Ryzhakov for providing samples of a series of N-oxides.

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Koldasheva, E.M., Geletii, Y.V., Yanilkin, V.V. et al. Electrogenerated cation radicals of heteroaromatic N-oxides and oxidation of cyclohexane induced by them. Russ Chem Bull 39, 886–890 (1990). https://doi.org/10.1007/BF00961675

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  • DOI: https://doi.org/10.1007/BF00961675

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