Abstract
cis-Myrtanethiol and a mixture of diastereoisomeric myrtanethiols were synthesized starting from (-)-β-pinene. Their oxidation with chlorine dioxide afforded a number of derivatives such as disulfides, S-thiol-sulfonates, sulfonyl chlorides, and sulfonic acids. The effects of reaction conditions (solvent nature, reactant molar ratio, reaction time, catalyst) on the yield and ratio of the products were studied. The corresponding sulfonyl chloride was obtained in quantitative yield by oxidation of thiol in the presence of vanadyl acetyl-acetonate, and optimal conditions were found for quantitative formation of myrtanesulfonic acid.
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Acknowledgments
The spectral and analytical data were obtained using the facilities of the “Chemistry” joint center at the Institute of Chemistry, Komi Scientific Center (Ural Branch, Russian Academy of Sciences).
Funding
This study was financially supported by the Ural Branch of the Russian Academy of Sciences (project no. 18-3-3-17).
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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, vol. 55, No. 10, pp. 1510–1519.
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Grebyonkina, O.N., Lezina, O.M., Izmest’ev, E.S. et al. Synthesis and Oxidation of Myrtanethiol and Its Functional Derivatives with Chlorine Dioxide. Russ J Org Chem 55, 1469–1475 (2019). https://doi.org/10.1134/S107042801910004X
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DOI: https://doi.org/10.1134/S107042801910004X