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Synthesis, Structure, and Chemical Transformations of 2-Chloroprop-2-en-1-yl Sulfones

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Abstract

A green approach was proposed for the synthesis of 2-chloroprop-2-en-1-yl sulfones in 47–94% yield. The molecular and crystal structures of 2-chloroprop-2-en-1-yl phenyl sulfone and 2-chloroprop-2-en-1-yl methyl sulfone were determined by X-ray analysis. π-Stacking interaction between the benzene ring and double bond was revealed in the crystal structure of 2-chloroprop-2-en-1-yl phenyl sulfone. Chloropropenyl sulfones were found to readily undergo dehydrochlorination to give stable allenyl sulfones and alkaline hydrolysis to produce the corresponding acetonyl sulfones. The latter can be converted to oximes by treatment with hydroxylamine hydrochloride.

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Acknowledgments

This study was performed using the facilities of the Baikal Joint Analytical Center, Siberian Branch, Russian Academy of Sciences.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033, Russia

    V. S. Nikonova, A. R. Kaliev, T. N. Borodina, V. I. Smirnov, I. B. Rozentsveig & N. A. Korchevin

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  1. V. S. Nikonova
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  2. A. R. Kaliev
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  3. T. N. Borodina
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  4. V. I. Smirnov
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  5. I. B. Rozentsveig
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  6. N. A. Korchevin
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Corresponding author

Correspondence to V. S. Nikonova.

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Conflict of Interests

The authors declare the absence of conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 12, pp. 1926–1932.

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Nikonova, V.S., Kaliev, A.R., Borodina, T.N. et al. Synthesis, Structure, and Chemical Transformations of 2-Chloroprop-2-en-1-yl Sulfones. Russ J Org Chem 55, 1912–1917 (2019). https://doi.org/10.1134/S1070428019120170

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  • DOI: https://doi.org/10.1134/S1070428019120170

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