Russian Journal of Organic Chemistry

, Volume 42, Issue 2, pp 190–192 | Cite as

Stereoselective addition of diorganyl chalcogenides to cyclohexene catalyzed with tin(IV) chloride

Article

Abstract

The addition of diorganyl disulfides and dimethyl diselenide to cyclohexene in the presence of tin(IV) chloride proceeded stereoselectively affording trans-adducts of 1:1 composition. No reaction occurs in the absence of tin(IV) chloride.

Keywords

Chloride Organic Chemistry Dimethyl Disulfide Cyclohexene 

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References

  1. 1.
    Caserio, M.J., Fisher, C.L., and Kim, Jhong, K., J. Org. Chem., 1985, vol. 50, p. 4390.CrossRefGoogle Scholar
  2. 2.
    Usugi, S.-i., Yorimitsu, H., Shinokubo, H., and Oshima, K., Org. Lett., 2004, vol. 6, p. 601.CrossRefGoogle Scholar
  3. 3.
    Kitamura, T., Matsuyuki, J., and Taniguchi, H., J. Chem. Soc., Perkin Trans. I, 1991, p. 1607.Google Scholar
  4. 4.
    Nikitina, L.E., Plemenkov, V.V., Chernov, A.N., Litvinov, I.A., and Kataeva, O.N., Zh. Obshch. Khim., 1990, vol. 60, p. 2303.Google Scholar
  5. 5.
    Kondo, T., Uenoyama, S., Fujita, K., and Mitsudo, T., J. Am. Chem. Soc., 1999, vol. 121, p. 482.Google Scholar
  6. 6.
    Hermans, B., Colard, N., and Hevesi, L., Tetrahedron Lett., 1992, vol. 33, p. 4629.CrossRefGoogle Scholar
  7. 7.
    Potapov, V.A., Amosova, S.A., Doron’kina, I.V., Starkova, A.A., and Hevesi, L., Sulfur Lett., 2002, vol. 25, p. 101.Google Scholar
  8. 8.
    Katrizky, A.R., Mayer, R., Morgenstern, J., and Sewell, M.J., J. Chem. Soc., 1965, p. 5953.Google Scholar
  9. 9.
    Shostakovskii, M.F., Prilezhaeva, E.N., Tsymbal, L.V., and Stolyarova, L.G., Zh. Obshch. Khim., 1960, vol. 30, p. 3143.Google Scholar
  10. 10.
    Parham, W.E., Motter, R.F., and Mayo, G.L.O., J. Am. Chem. Soc., 1959, vol. 81, p. 3386.Google Scholar
  11. 11.
    Kuniyasu, H., Ogawa, A., Miyazaki, S.-I., Ryu, I., Kambe, N., and Sonoda, N., J. Am. Chem. Soc., 1991, vol. 113, p. 9796.CrossRefGoogle Scholar
  12. 12.
    Potapov, V.A. and Amosova, S.V., Zh. Org. Khim., 2003, vol. 39, p. 1449.Google Scholar
  13. 13.
    De, Filippo, D. and Momicchiolli, F., Tetrahedron, 1969, vol. 25, p. 5733.Google Scholar

Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • A. V. Martynov
    • 1
  • A. R. Zhinkin
    • 1
  • S. V. Amosova
    • 1
  1. 1.Faworsky Irkutsk Institute of Chemistry, Siberian DivisionRussian Academy of SciencesIrkutskRussia

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