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Electrosynthesis of Mono- and Disulfides Based on C5–C8 Cycloalkanes, Hydrogen Sulfide, and Isomeric Dibutyl Disulfides

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Abstract

A method of synthesis of organic mono-, di-, and polysulfides based on electrochemical reactions of unsubstituted and alkyl–substituted cycloalkanes C5–C8 with di(n-butyl)disulfide (di(tert-butyl)disulfide) and hydrogen sulfide is developed. Three–component electrosynthesis is carried out in methylene chloride under atmospheric pressure, at the room temperature under the conditions of anodic H2S activation to a cation radical fragmented to a proton and a thiyl radical. The suggested approach with application of oxidative conversion initiation allows obtaining asymmetric mono-, disulfides and symmetric disulfides. The yield of biologically active organic sulfur derivatives depends on the electrosynthesis duration, structure of isomeric dibutyl sulfides, alicycle size and saturation degree.

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Funding

The study is supported by the Russian Foundation for Basic Research (project no. 17-13-01168).

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Authors and Affiliations

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

    E. V. Shinkar’, A. V. Shvetsova, A. O. Okhlobystin & N. T. Berberova

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  1. E. V. Shinkar’
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  2. A. V. Shvetsova
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  3. A. O. Okhlobystin
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  4. N. T. Berberova
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Correspondence to E. V. Shinkar’ or N. T. Berberova.

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Translated by M. Ehrenburg

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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Shinkar’, E.V., Shvetsova, A.V., Okhlobystin, A.O. et al. Electrosynthesis of Mono- and Disulfides Based on C5–C8 Cycloalkanes, Hydrogen Sulfide, and Isomeric Dibutyl Disulfides. Russ J Electrochem 56, 285–292 (2020). https://doi.org/10.1134/S1023193520040138

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