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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The study is supported by the Russian Foundation for Basic Research (project no. 17-13-01168).
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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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DOI: https://doi.org/10.1134/S1023193520040138