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An ene-type reaction between an unactivated olefin and an “activated” sulfoxide, and some properties of the resulting sulfonium salts

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

Conclusions

  1. 1.

    Using DMSO and MeSOPh it has been shown for the first time that O-trifluoroacetylated sulfoxides react with unactivated trisubstituted olefins to give allylsulfonium salts.

  2. 2.

    LiClO4 has been found to accelerate this ene-type reaction.

  3. 3.

    It has been found for the first time in the aliphatic series that the competition between [3, 2]-rearrangement and the Stevens rearrangement of the S-ylid generated from the allylsulfonium salt is governed by the type of counterion present, and this observation has been rationalized.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    A. M. Moiseenkov, V. A. Dragan & V. V. Veselovskii

Authors
  1. A. M. Moiseenkov
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  2. V. A. Dragan
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  3. V. V. Veselovskii
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 365–372, February, 1989.

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Moiseenkov, A.M., Dragan, V.A. & Veselovskii, V.V. An ene-type reaction between an unactivated olefin and an “activated” sulfoxide, and some properties of the resulting sulfonium salts. Russ Chem Bull 38, 314–319 (1989). https://doi.org/10.1007/BF00953620

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  • DOI: https://doi.org/10.1007/BF00953620

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