Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

α-Methyl-α-chloro-β-propiothiolactone in the synthesis of derivatives of thioglycidic acid

  • 22 Accesses

  • 2 Citations

Conclusions

  1. 1.

    The piperidide and the methyl ester ofα-methyl-α,β-thioglycidic acid have been prepared.

  2. 2.

    Amides ofα-methyl-α,β-thioglycidic acid are readily cleaved by chlorine to form preferentiallyβ-chloro-α-sulfenchlorides.

  3. 3.

    Besides having the usual properties of thiiranes, amides ofα-methyl-α,β-thioglycidic acid are characterized by the fact that under the influence of traces of piperidine they redistribute the sulfur to form amides of methacrylic acid and disulfides.

This is a preview of subscription content, log in to check access.

Literature cited

  1. 1.

    C. C. J. Culvenor, W. Davies, and K. H. Pausacker, J. Chem. Soc., 1050 (1946).

  2. 2.

    C. C. J. Culvenor, W. Davies, and N. S. Heath, J. Chem. Soc., 278 (1949).

  3. 3.

    C. C. J. Culvenor, W. Davies, J. A. MacLaven, P. F. Nelson, and W. E. Savige, J. Chem. Soc., 2573 (1949).

  4. 4.

    J. A. Durden, Jr., H. A. Stausbury, Jr., and W. A. Catlette, J. Amer. Chem. Soc.,81, 1943 (1959).

  5. 5.

    T. C. Owen, C. L. Gladis, and L. Field, J. Chem. Soc., 501 (1962).

  6. 6.

    T. C. Owen, C. L. Gladis, and L. Field, J. Chem. Soc., 656 (1962).

  7. 7.

    A. S. V. Choughuley and M. S. Chadha, Indian J. Chem.,1, 437 (1963).

  8. 8.

    C. C. Tung and A. J. Speziale, J. Org. Chem.,29, 1577 (1964).

  9. 9.

    A. J. Speziale and C. C. Tung, J. Org. Chem.,28, 1353 (1963).

  10. 10.

    A. Schönberg, D. Cernic, and W. Urban, Chem. Ber.,64, 2579 (1931).

  11. 11.

    W. J. Middleton, USA Patent No. 3136781, Chem. Abstrs.,61, 5612 (1964).

  12. 12.

    A. M. Orlov, N. D. Kuleshova, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 1400 (1967).

  13. 13.

    U. Hasserodt, Chem. Ber.,100, 1482 (1967).

  14. 14.

    M. G. Lin'kova, D. I. Greichute, Z. A. Stumbrevichute, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 1872 (1968).

  15. 15.

    M. M. Kotort, G. A. Sokolova, M. N. Savitskaya, and T. M. Kiseleva, Zh. Obshch. Khim.,27, 2239 (1957).

Download references

Author information

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1148–1153, May, 1969.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Lin'kova, M.G., Orlov, A.M., Kil'disheva, O.V. et al. α-Methyl-α-chloro-β-propiothiolactone in the synthesis of derivatives of thioglycidic acid. Russ Chem Bull 18, 1048–1053 (1969). https://doi.org/10.1007/BF00922869

Download citation

Keywords

  • Sulfur
  • Methyl
  • Ester
  • Amide
  • Chlorine