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Directed oxidative coupling of thiols in the synthesis of unsymmetrical disulfides

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Abstract

Oxidative coupling of two different thiols bearing aliphatic, alicyclic, aromatic, and hetero-aromatic moieties promoted by mild oxidizing agents, viz., sterically hindered o-benzo(imino)-quinones, carried out in N-methylpyrrolidone at room temperature led to unsymmetrical disulfides. Among the studied oxidizers, the most active was 3,6-di-tert-butyl-o-benzoquinone, which, in contrast to 3,5-di-tert-butyl-o-benzoquinone, was not involved in the Michael addition. Under the optimal reaction conditions, the yields of the target unsymmetrical disulfides reach 81%.

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Authors and Affiliations

  1. Astrakhan State Technical University, 16 ul. Tatishcheva, 414056, Astrakhan, Russian Federation

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

  2. Federal Research Center the Southern Scientific Center of the Russian Academy of Sciences, 41 prosp. Chekhova, 344006, Rostov-on-Don, Russian Federation

    I. V. Smolyaninov

Authors
  1. D. A. Burmistrova
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  2. I. V. Smolyaninov
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  3. N. T. Berberova
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Corresponding author

Correspondence to D. A. Burmistrova.

Additional information

This work was financially supported by the Russian Foundation for Basic Research (Project No. 18-29-24001).

Based on the materials of the XXI Mendeleev Congress on General and Applied Chemistry (September 9-13, 2019, St. Petersburg, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 0990–0995, May, 2020.

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Burmistrova, D.A., Smolyaninov, I.V. & Berberova, N.T. Directed oxidative coupling of thiols in the synthesis of unsymmetrical disulfides. Russ Chem Bull 69, 990–995 (2020). https://doi.org/10.1007/s11172-020-2860-1

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