Skip to main content
Log in

Thermal hydrothiolysis of di(2-thienyl)sulfide in the gaseous and liquid phase

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

At 500–600‡, di(2-thienyl)sulfide is converted to thiophene, thiophene thiols, dithienyls, and dithienothiophenes, and isomerized to 2,3-dithienylsulfide. Hydrogen sulfide accelerates these reactions significantly. In the liquid phase the thermal conversion of di(2-thienyl)sulfide takes place only with the participation of elemental sulfur or in the system sulfur-hydrogen sulfide. Thiophene and diethienothiophenes are not formed in this case, while isomerization occurs to a large degree. The observed thermal conversions of di(2-thienyl)-sulfide are based on the addition of thiyl radicals to the double bonds of the thiophene ring and to the sulfide sulfur atom.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature Cited

  1. L. K. Papernaya, G. M. Panova, é. N. Deryagina, and M. G. Voronkov, Zh. Org. Khim., 22, 1975 (1986).

    Google Scholar 

  2. M. G. Voronkov, é. N. Deryagina, L. G. Klochkova, and A. S. Nakhmanovich, Zh. Org. Khim., 12, 1515 (1976).

    Google Scholar 

  3. W. H. Houff and R. D. Schuetz, J. Am. Chem. Soc., 75, 6316 (1953).

    Google Scholar 

  4. M. G. Rudenko and V. N. Gromova, Dokl. Akad. Nauk SSSR, 81, 207 (1951).

    Google Scholar 

  5. I. N. Tits-Skvortsova, A. I. Leonova, and S. Ya. Levina, Zh. Org. Khim., 23, 30, 303 (1953).

    Google Scholar 

  6. F. A. Davis, T. W. Paminto, S. B. Awad, and R. L. Billmers, J. Org. Chem., 49, 1228 (1984).

    Google Scholar 

  7. R. D. Obolentsev and Yu. E. Nikitin, in: The Chemistry of Organic Sulfur Compounds Present in Crude Oil and Petroleum Products [in Russian], Vysshaya Shkola, Moscow (1968) Vol. 8, p. 163.

    Google Scholar 

  8. A. S. Dneprovskii and T. I. Temnikova, Theoretical Foundations of Organic Chemistry [in Russian], Khimiya, Leningrad (1979), p. 190.

    Google Scholar 

  9. D. Nonhuebel and G. Walton, The Chemistry of Free Radicals [Russian translation], Mir, Moscow (1977), p. 407.

    Google Scholar 

  10. M. G. Voronkov, é. N. Deryagina, E. N. Sukhomazova, O. I. Randin, V. V. Keiko, and I. D. Kalikhman, Khim. Geterotsikl. Soedin., No. 9, 1186 (1976).

    Google Scholar 

  11. E. Profft and J. Solf, J. Pr. Chem., 24, 38 (1964).

    Google Scholar 

  12. C. D. Hurd and H. J. Anderson, J. Am. Chem. Soc., 75, 3517 (1953).

    Google Scholar 

  13. M. G. Voronkov, é. N. Deryagina, é. N. Sukhomazova, N. A. Korchevin, L. V. Klyba, and M. V. Sigalov, Khim. Geterotsikl. Soedin., No. 8, 1134 (1985).

    Google Scholar 

  14. V. V. Mikhailik, Yu. V. Razkazovskii, and M. Ya. Mel'nikov, Dokl. Akad. Nauk SSSR, 263, 934 (1982).

    Google Scholar 

  15. J. R. M. Giles and B. P. Roberts, J. Chem. Soc. Perkin 1, No. 10, 1497 (1980).

    Google Scholar 

  16. Yu. G. Poltavtsev and Yu. V. Titenko, Zh. Fiz. Khim., 49, 301 (1975).

    Google Scholar 

  17. M. G. Voronkov, N. S. Vyazankin, é. N. Deryagina, A. S. Nakhmanovich, and V. A. Usov, Reactions of Sulfur with Organic Compounds [in Russian], Nauka, Siberian Branch, Novosibirsk (1979), p. 40.

    Google Scholar 

  18. M. G. Voronkov, é. D. Deryagina, é. N. Sukhomazova, A. N. Mirskova, and S. G. Seredkina, Zh. Org. Khim., 19, 1641 (1983).

    Google Scholar 

  19. G. F. Bol'shakova and E. A. Glebovskaya, Frequency Tables of Infrared Spectra of Heteroorganic Compounds [in Russian], Khimiya, Leningrad (1968), p. 62.

    Google Scholar 

  20. E. Jones and I. M. Modie, Tetrahedron, 21, 2413 (1965).

    Google Scholar 

  21. F. Jong and M. J. Janssen, J. Org. Chem., 36, 1645 (1971).

    Google Scholar 

  22. F. Jong and M. J. Janssen, J. Org. Chem., 36, 1998 (1971).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Communication 29 of the series “High-temperature organic synthesis.” For Communication 28 see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1614–1619, December, 1986.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Voronkov, M.G., Deryagina, E.N., Papernaya, L.K. et al. Thermal hydrothiolysis of di(2-thienyl)sulfide in the gaseous and liquid phase. Chem Heterocycl Compd 22, 1301–1306 (1986). https://doi.org/10.1007/BF00474348

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00474348

Keywords

Navigation