Skip to main content
SpringerLink
Log in

Products of Reaction of Tricyclo[4.1.0.02,7]heptane and 1-Bromotricyclo[4.1.0.02,7]heptane with Hydrogen Sulfide, and Syntheses Based Thereon

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

By reactions of 1-R-tricyclo[4.1.0.02,7]heptanes (R = H, Br) with hydrogen sulfide initiated by UV irradiation endo-6-bicyclo[3.1.1]heptanethiols and bis(endo-6-bicyclo[3.1.1]heptyl) sulfides were synthesized. The sulfides were oxidized to the corresponding sulfoxides and sulfones. The results of HBr elimination from the bromine-substituted sulfoxides and sulfones effected by potassium tert-butylate are discussed. The latter reaction results in the recovery of the system of 1-substituted tricyclo[4.1.0.02,7]heptane.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Pryor, W.A. Mechanisms of Sulfur Reactions, New York: McGraw-Hill Book Company, INC, 1962; Poluchenie i svoistva organicheskikh soedinenii sery (Synthesis and Properties of Sulfur Organic Compounds), Belen'kii, L.I., Ed., Moscow: Khimiya, 1998.

    Google Scholar 

  2. Vasin, V.A., Zh. Org. Khim., 1995, vol. 31, no. 9, pp. 1393-1407.

    Google Scholar 

  3. Szeimies, G., Schlober, A., Philipp, F., Dietz, P., and Mickler, W., Chem. Ber., 1978, vol. 111, no. 5, pp. 1922-1937.

    Google Scholar 

  4. Vasin, V.A., Bolusheva, I.Yu., Chernyaeva, L.V., Tanaseichuk, B.S., Surmina, L.S., and Zefirov, N.S., Zh. Org. Khim., 1990, vol. 26, no. 7, pp. 1509-1515.

    Google Scholar 

  5. Vasin, V.A., Kostryukov, S.G., Razin, V.V., Bolusheva, I.Yu., and Zefirov, N.S., Zh. Org. Khim., 1994, vol. 30, no. 9, pp. 1351-1359.

    Google Scholar 

  6. Vasin, V.A., Kostryukov, S.G., Romanova, E.V., Bolusheva, I.Yu., and Razin, V.V., Zh. Org. Khim., 1996, vol. 32, no. 11, pp. 1701-1708.

    Google Scholar 

  7. Wiberg, K.B. and Hess, B.A., J. Org. Chem., 1966, vol. 31, no. 7, pp. 2250-2254.

    Google Scholar 

  8. Vasin, V.A., Kostryukov, S.G., Bolusheva, I.Yu., and Razin, V.V., Zh. Org. Khim., 1993, vol. 29, no. 7, pp. 1349-1357.

    Google Scholar 

  9. Lockard, J.P., Schroeck, W.C., and Johnson, C.R., Synthesis, 1973, p. 485.

  10. The Aldrich Library of 13 C and 1 H FT-NMR Spectra. Aldrich, 2000–2001. FT-NMR 1 (1), 1417 B.

  11. Razin, V.V., Eremenko, M.V., and Ogloblin, K.A., Zh. Org. Khim., 1978, vol. 14, no. 5, pp. 973-979.

    Google Scholar 

  12. Szeimies, G., Philipp, F., Baumgartel, O., and Harnisch, I., Tetrahedron Lett., 1977, vol. 18, no. 25, pp. 2135-2138.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Mordovian Ogarev State University, Saransk, 430000, Russia

    V. A. Vasin & S. G. Kostryukov

  2. St. Petersburg State University, St. Petersburg, 198904, Russia

    V. V. Razin

Authors
  1. V. A. Vasin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. G. Kostryukov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. V. Razin
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vasin, V.A., Kostryukov, S.G. & Razin, V.V. Products of Reaction of Tricyclo[4.1.0.02,7]heptane and 1-Bromotricyclo[4.1.0.02,7]heptane with Hydrogen Sulfide, and Syntheses Based Thereon. Russian Journal of Organic Chemistry 38, 1582–1587 (2002). https://doi.org/10.1023/A:1022597614806

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1022597614806

Keywords

Search

Navigation