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Chemistry of Heterocyclic Compounds

, Volume 9, Issue 1, pp 6–9 | Cite as

Isomerization of β-halo disulfides (alkyl 2-haloethyl disulfides)

  • N. M. Karimova
  • M. G. Lin'kova
  • O. V. Kil'disheva
  • I. L. Knunyants
Article
  • 23 Downloads

Abstract

The methyl ester, amide, dimethylamide, and anilide of α-methylthioglycidic acid are readily cleaved by methane and acetylsulfenyl chlorides to give mixtures of the corresponding isomeric cleavage products — vicinal chlorodithio derivatives of isobutyric acid. It is shown that the ratio of isomers obtained depends both on the character of the substituent in the carboxyl group of the isobutyric acid and on the character of the substituent attached to the sulfur atom in the sulfenyl chloride (sulfomonochloride) used. It was found that β-halo disulfides, like β-halo sulfides, are capable of isomerization.

Keywords

Sulfur Methyl Chloride Ester Methane 
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.
    Organic Sulfur Compounds, Vol. 1, London (1961), p. 257.Google Scholar
  2. 2.
    W. A. Thaler, W. H. Mueller, and P. E. Butler, J. Am. Chem. Soc., 90, 2069 (1968).Google Scholar
  3. 3.
    W. H, Mueller, Angew. Chem., 8, 482 (1969).Google Scholar
  4. 4.
    M. G. Lin'kova, L. P. Parshina, Z. M. Stumbravichute, O. V. Kil'disheva, and I. L. Knunyants, Dokl. Akad. Nauk SSSR, 196, 1089 (1971).Google Scholar
  5. 5.
    M. G. Lin'kova, D. I. Greichute, L. P. Rasteikene, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 2522 (1971).Google Scholar
  6. 6.
    N. V. Schwartz, J. Org. Chem., 33, 2895 (1968).Google Scholar
  7. 7.
    N. M, Karimova, M. G. Lin'kova, O. V. Kil'disheva, and I. L. Knunyants, Khim. Geterotsikl. Soedin., 475 (1972).Google Scholar
  8. 8.
    M. G. Lin'kova, A. M. Orlov, O. V. Kil'disheva, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 1148 (1969).Google Scholar
  9. 9.
    L. P. Parshina, M. G. Lin'kova, O. V. Kil'disheva, and I. L. Knunyants, Izv. Akad. Nauk SSSR, 931 (1970).Google Scholar

Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1975

Authors and Affiliations

  • N. M. Karimova
    • 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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