Chemistry of Heterocyclic Compounds

, Volume 12, Issue 7, pp 745–748 | Cite as

Synthesis of 2-thiabicyclo[3.2.0]hept-3-enes by reaction of acetylene with sodium sulfide

  • B. A. Trofimov
  • G. A. Kalabin
  • V. V. Kryuchkov
  • V. V. Keiko
  • S. V. Amosova
  • V. M. Bzhezovskii
  • V. K. Voronov
  • D. F. Kushnarev
  • V. Yu. Vitkovskii
  • L. I. Lavlinskaya
  • V. A. Pestunovich
Article

Abstract

The previously unknown2-thiabicyclo[2.3.0]hept-3-ene and exo- and endo-6-methyl-2-thiabicyclo[3.2.0]hept-3-enes were synthesized in one step from acetylene and sodium sulfide in aqueous dimethyl disulfoxide.

Keywords

Sodium Sulfide Organic Chemistry Dimethyl Acetylene 
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.
    B. A. Trofimov (Trofimow) and S. V. Amosova (Amosowa), West German Patent No. 2260434 (1974).Google Scholar
  2. 2.
    G. A. Kalabin, B. A. Trofimov, S. V. Amosova, and V. K. Voronov, Khim. Getertosikl. Soedin., No. 5, 606 (1975).Google Scholar
  3. 3.
    B. A. Trofimov, S. V. Amosova, and V. K. Voronov, USSR Author's Certificate No. 405898; Byul. Izobr., No. 45, 98 (1973).Google Scholar
  4. 4.
    L. Bellamy, New Data on the Infrared Spectra of Complex Molecules [Russian translation], Moscow (1971), pp. 28, 41.Google Scholar
  5. 5.
    M. F. Shostakovskii, A. S. Atavin, S. V. Amosova, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1852 (1968).Google Scholar
  6. 6.
    I. Fabian, H. Kröber, and R. Mayer, Spectrochim. Acta, 24A, 727 (1968).Google Scholar
  7. 7.
    I. H. Bowie, R. G. Cooks, S. -O. Lawesson, and C. Nolde, J. Chem. Soc., B, 616 (1967).Google Scholar
  8. 8.
    V. Hanuš and V. Čermak, Coll. Czech. Chem. Commun., 24, 1602 (1959).Google Scholar
  9. 9.
    I. Ceccarelli and E. Chiellini, Org. Magn. Res., 2, 409 (1970).Google Scholar
  10. 10.
    A. S. Atavin, A. I. Mikhaleva, B. A. Trofimov, G. A. Kalabin, and I. P. Vasil'ev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 614 (1971).Google Scholar
  11. 11.
    B. A. Trofimov, S. V. Amosova, A. S. Atavin, G. A. Kalabin, N. K. Gusarova, and M. V. Ivanova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1947 (1971).Google Scholar
  12. 12.
    A. S. Atavin, A. I. Mikhaleva, V. A. Pestunovich, E. G. Chebotareva, V. P. Kaigorodova, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2334 (1973).Google Scholar
  13. 13.
    W. Brügel, Nuclear Magnetic Resonance Spectra and Chemical Structure, Vol. 1, Academic Press, New York-London (1967), p. 180.Google Scholar
  14. 14.
    R. I. Abraham, M. A. Cooper, I. R. Salmon, and D. Whittaker, Org. Magn. Res., 4, 489 (1972).Google Scholar
  15. 15.
    B. A. Trofimov, S. V. Amosova, O. A. Tarasova, V. V. Keiko, and V. K. Voronov, Zh. Org. Khim., 10, 127 (1974).Google Scholar
  16. 16.
    B. A. Trofimov, S. V. Amosova, N. K. Gusarova, O. A. Tarasova, and M. G. Voronkov, Zh. Org. Khim., 11, 2225 (1975).Google Scholar

Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • B. A. Trofimov
    • 1
  • G. A. Kalabin
    • 1
  • V. V. Kryuchkov
    • 1
  • V. V. Keiko
    • 1
  • S. V. Amosova
    • 1
  • V. M. Bzhezovskii
    • 1
  • V. K. Voronov
    • 1
  • D. F. Kushnarev
    • 1
  • V. Yu. Vitkovskii
    • 1
  • L. I. Lavlinskaya
    • 1
  • V. A. Pestunovich
    • 1
  1. 1.Irkutsk Institute of Organic ChemistrySiberian Branch of the Academy of Sciences of the USSRUSSR

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