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Mechanism of autoreduction of 2,2,6,6-tetramethyl-1,4-dioxopiperidinium cation in alkaline medium

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Abstract

Autoreduction of 2,2,6,6-tetramethyl-1,4-dioxopiperidinium ion to nitroxyl radical in alkaline medium involves a number of parallel and consecutive reactions. The primary products of the reaction of 2,2,6,6-tetramethyl-1,4-dioxopiperidinium with hydroxide ion are three nitroso compounds and N-hydroxy-2,2,6,6-tetramethylpiperidine N-oxide. Isomerization of the nitroso compounds and elimination of acetone from the N-oxide give cyclic hydroxylamines which reduce the initial cation to nitroxyl radical, being oxidized to nitrones.

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Authors and Affiliations

  1. Institute of Chemical Physics Problems, Russian Academy of Sciences, pr. Akad. Semenova 1, Chernogolovka, Moscow oblast, 142432, Russia

    V. A. Golubev & V. D. Sen’

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  1. V. A. Golubev
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  2. V. D. Sen’
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Correspondence to V. D. Sen’.

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Original Russian Text © V.A. Golubev, V.D. Sen’, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 6, pp. 854–861.

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Golubev, V.A., Sen’, V.D. Mechanism of autoreduction of 2,2,6,6-tetramethyl-1,4-dioxopiperidinium cation in alkaline medium. Russ J Org Chem 47, 869–876 (2011). https://doi.org/10.1134/S1070428011060066

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  • DOI: https://doi.org/10.1134/S1070428011060066

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