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Mechanism of the photochemical chlorination of sulfones

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The photochlorination of dimethylsulfone proceeds according to a radical-chain mechanism with cleavage of a C-H bond and formation of trichloromethylmethylsulfone as the only product.

  2. 2.

    Photochlorination of diethylsulfone at the first step also proceeds with cleavage of a C-H bond, but the radical C2H5SO2CH2CH2 formed in this case is stabilized by cleavage of a C-S bond, forming ethylene and the radical C2H5SO2.

  3. 3.

    Photochlorination of methylphenylsulfone proceeds according to a mechanism analogous to that for diphenyl- and dimethylsulfones.

  4. 4.

    Photochlorination of sulfolane proceeds according to a radical-chain mechanism with cleavage of the C-H bond at theβ-carbon atom, forming 3,3,4,4-tetrachlorosulfolane as the final product.

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Literature cited

  1. V. I. Dronov, V. A. Snegotskaya, L. P. Ivanova, and N. N. Bannikova, in: The Chemistry of Organosulfur Compounds Contained in Petroleums and Petroleum Products [in Russian], Vol. 9, Vysshaya Shkola (in press).

  2. V. I. Dronov and V. A. Snegotskaya, in: The Chemistry of Organosulfur Compounds Contained in Petroleum and Petroleum Products [in Russian], Vol. 8, Vysshaya Shkola (1968).

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  5. Dictionary of Organic Compounds [Russian translation], Vol. 2, IL (1949), p. 12.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Bashkir Branch of the Academy of Sciences of the USSR, USSR

    V. I. Dronov & V. A. Snegotskaya

Authors
  1. V. I. Dronov
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  2. V. A. Snegotskaya
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2029–2032, September, 1970.

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Dronov, V.I., Snegotskaya, V.A. Mechanism of the photochemical chlorination of sulfones. Russ Chem Bull 19, 1907–1910 (1970). https://doi.org/10.1007/BF00849770

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  • DOI: https://doi.org/10.1007/BF00849770

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