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Redox Properties and Reactivity of Organic Trisulfides in Reactions with Alkenes

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Abstract

The redox reactions of organic trisulfides containing various hydrocarbon groups with alkenes in aprotic solvents were studied. The electrooxidation of trisulfides proceeds irreversibly by the ECE mechanism, with formation of sulfur-centered RS+ and RSS+ intermediates. The generated cations enter into electrophilic addition reactions with alkenes, forming asymmetric di- and monosulfides. The electrochemical reduction of trisulfides leads to the formation of a radical anion, which is fragmented into the RSS anion and RS radical. In the presence of acetic acid, the cathodic activation of trisulfides is accompanied by the formation of alkyl and phenyl hydrodisulfides (RSSH).

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Funding

This study was financially supported by the Russian Science Foundation (project no. 17-13-01168).

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Authors and Affiliations

  1. Astrakhan State Technical University, 414056, Astrakhan, Russia

    D. A. Burmistrova, I. V. Smolyaninov & N. T. Berberova

  2. Southern Research Center, Russian Academy of Sciences, 344006, Rostov-on-Don, Russia

    I. V. Smolyaninov

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  1. D. A. Burmistrova
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Translated by L. Smolina

Published on the basis of materials of the XIX All-Russian Conference “Electrochemistry of Organic Compounds” (EKHOS-2018) (with international participation), Novocherkassk, 2018.

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Burmistrova, D.A., Smolyaninov, I.V. & Berberova, N.T. Redox Properties and Reactivity of Organic Trisulfides in Reactions with Alkenes. Russ J Electrochem 56, 329–336 (2020). https://doi.org/10.1134/S1023193520040035

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