Conclusions
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1.
The first stage of the electroreduction of aryl- and adamantylnitrile oxides corresponds to a transfer of one electron with the formation of anion radicals, whose stability is determined by the structure of the starting material.
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2.
In aqueous DMF, the electrolysis at one-electron reduction wave potentials of mesitylenenitrile oxide, and also the electrolysis at two-electron reduction wave potentials of dimesitylfuroxane lead to the formation of dimethylglyoxime anion.
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3.
EPR spectra of stable anion radicals of p- and m-nitrobenzonitrile oxides were recorded for the first time.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 281–286, February, 1989.
The authors wish to express their deep gratitude to L. I. Khmel'nitskii, T. I. Godovikova, and O. A. Rakitin for their participation in the discussion of the results of the present work, and for kindly providing the starting materials.
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Sosonkin, I.M., Domarev, A.N., Kuznetsova, A.L. et al. Study of electrochemical behavior of nitrile N-oxides. Russ Chem Bull 38, 235–239 (1989). https://doi.org/10.1007/BF00953603
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DOI: https://doi.org/10.1007/BF00953603