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Synthesis and oxidation of sulfides based on (–)-caryophyllene oxide and tert-butanethiol

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Abstract

An acid-catalyzed reaction of (–)-caryophyllene oxide with tert-butanethiol led to sulfides with the clovane structure of the sesquiterpene fragment in up to 63% yields. The oxidation of these sulfides gave sulfoxides in up to 38% yields (de 59%) and sulfones in up to 89%.

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Authors and Affiliations

  1. Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences, 48 ul. Pervomaiskaya, 167982, Syktyvkar, Russian Federation

    J. W. Gyrdymova, E. S. Izmest´ev, S. A. Rubtsova & A. V. Kutchin

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  1. J. W. Gyrdymova
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  2. E. S. Izmest´ev
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  3. S. A. Rubtsova
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  4. A. V. Kutchin
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Correspondence to J. W. Gyrdymova.

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Dedicated to Academician of the Russian Academy of Sciences O. G. Sinyashin on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1238–1242, May, 2016.

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Gyrdymova, J.W., Izmest´ev, E.S., Rubtsova, S.A. et al. Synthesis and oxidation of sulfides based on (–)-caryophyllene oxide and tert-butanethiol. Russ Chem Bull 65, 1238–1242 (2016). https://doi.org/10.1007/s11172-016-1441-9

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  • DOI: https://doi.org/10.1007/s11172-016-1441-9

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