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Chlorolysis of 1,2-dithiolan-3-ones,1,2-dithiol-4-en-3-ones, and acetyl alkyl disulfides

  • T. P. Vasil'eva
  • M. G. Lin'kova
  • O. V. Kil'disheva
  • I. L. Knunyants
Organic and Biological Chemistry

Conclusions

  1. 1.

    The direction of the chlorolysis of acyl alkyl disulfides depends on the character of the alkyl radical, and can go with a cleavage of the S-S bond, the S-CO bond, or with a simultaneous cleavage of both bonds. The probability of cleaving the S-CO bond increases with increase in the electronegativity of the alkyl radical.

     
  2. 2.

    The chlorolysis of 1,2-dithiolan-3-ones and 1,2-dithiol-4-en-3-ones by SO2Cl2 goes in an unambiguous manner, with a cleavage of the S-CO bond and the formation of heat stable acid chlorides ofβ-(chlorodisulfenyl)carboxylic acids.

     
  3. 3.

    The presence of electron-withdrawing substituents in both cyclic and open acyl alkyl disulfides hinders the chlorolysis.

     

Keywords

Chloride Disulfide Carboxylic Acid Acetyl Alkyl Radical 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

  1. 1.
    T. P. Vasil'eva, M. G. Lin'kova, O. V. Kil'disheva, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 2379 (1973); 700 (1974).Google Scholar
  2. 2.
    F. Boberg, Angew. Chem.,73, 579 (1961).Google Scholar
  3. 3.
    H. Böhme and G. Ham, Ann. Chem.,617, 62 (1958).Google Scholar
  4. 4.
    T. P. Vasil'eva, M. G. Lin'kova, O. V. Kil'disheva, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 209 (1973).Google Scholar

Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • T. P. Vasil'eva
    • 1
  • M. G. Lin'kova
    • 1
  • O. V. Kil'disheva
    • 1
  • I. L. Knunyants
    • 1
  1. 1.Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow

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