Skip to main content
SpringerLink
Log in

Epoxidation and Heterocyclization of Arenesulfonamides of the Norbornene Series

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

Abstract

Reactions of previously known and newly synthesized N-(bicyclo[2.2.1]hept-5-en-endo-2-ylmethyl)arenesulfonamides with monoperoxyphthalic acid generated in situ from phthalic anhydride and 30% hydrogen peroxide lead mostly to the corresponding N-arylsulfonyl-exo-2-hydroxy-4-azatricyclo[4.2.1.03,7]nonanes (azabrendanes). In some cases, N-(exo-5,6-epoxybicyclo[2.2.1]hept-5-en-exo-2-ylmethyl)arenesulfonamides were isolated as the only products or mixtures of alternative oxidation products were obtained. The presence of electron-acceptor nitro groups in the benzene ring and bulky substituents, primarily in the ortho position, is considered to be a structural factor preventing the primary oxidation products (epoxy derivatives) from undergoing heterocyclization.

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. Lewis, D.E. and Rigby, H.L., Tetrahedron Lett., 1985, vol. 26, p. 3437; Van Eycken, J., Vanderwalle, M., Heinemann, G., Laumen, K., Schneider, M.P., and Kredel, J., J. Chem. Soc., Chem. Commun., 1989, p. 306; Le Drian, C. and Vogel, P., Tetrahedron Lett., 1987, vol. 28, p. 1523; Le Drian, C. and Vogel, P., Helv. Chim. Acta, 1988, vol. 71, p. 1399.

    Article  CAS  Google Scholar 

  2. Kas'yan, L.I., Usp. Khim., 1998, vol. 67, p. 299; Prilezhaeva, E.N., Reaktsiya Prilezhaeva. Elektrofil'noe okislenie (Prilezhaev Reaction. Electrophilic Oxidation), Moscow: Nauka, 1974; Berty, G., Topics in Stereochemistry, Allinger, N.L. and Eliel, E.L., Eds., New York: Wiley, 1973, vol. 7, p. 93; Kas'yan, L.I., Seferova, M.F., and Okovityi, S.I., Alitsiklicheskie epoksidnye soedineniya. Metody sinteza (Alicyclic Epoxy Compounds. Methods of Synthesis), Dnepropetrovsk: Dnepropetr. Gos. Univ., 1996.

    Google Scholar 

  3. Henbest, H.B. and Nicholls, B., J. Chem. Soc., 1959, p. 221; Nazarov, I.N., Kucherov, V.F., and Bukharov, V.G., Izv. Akad. Nauk SSSR, Ser. Khim., 1958, p. 192; Giese, B., Chem. Ber., 1974, vol. 107, p. 808; Mehta, G., Padwa, S., Venkatesan, K., Begum, N.S., and Moorthy, J.N., Indian J. Chem., Sect. B, 1992, vol. 31, p. 473.

  4. Kasyan, L.I., Sereda, S.V., Potekhin, K.A., and Kasyan, A.O., Heteroatom Chem., 1997, vol. 8, p. 177.

    CAS  Google Scholar 

  5. Kas'yan, A.O., Maletina, I.I., Yagupol'skii, L.M., Markov, V.I., and Kas'yan, L.I., Russ. J. Org. Chem., 1995, vol. 31, p. 320.

    Google Scholar 

  6. Kas'yan, L.I., Tarabara, I.N., and Kas'yan, A.O., Russ. J. Org. Chem., 2002, vol. 38, p. 19.

    Google Scholar 

  7. Kas'yan, A.O., Isaev, A.K., and Kas'yan, L.I., Russ. J. Org. Chem., 2002, vol. 38, p. 553.

    Google Scholar 

  8. Kas'yan, L.I., Kas'yan, A.O., Gorb, L.G., and Klebanov, B.M., Russ. J. Org. Chem., 1995, vol. 31, p. 626; Kas'yan, A.O., Tarabara, I.N., Petrina, I.V, Karpenko, D.V., and Kas'yan, L.I., Vopr. Khim. Khim. Tekhnol., 2002, no. 4, p. 40.

    Google Scholar 

  9. Kas'yan, L.I., Krasnovskaya, O.Yu., and Kas'yan, A.O., Russ. J. Org. Chem., 1996, vol. 32, p. 1068; Kas'yan, A.O., Tarabara, I.N., Golodaeva, E.A., and Kas'yan, L.I., Russ. J. Org. Chem., 2001, vol. 37, p. 1659; Golodaeva, E.A., Kas'yan, A.O., Bakumov, V.A., and Kas'yan, L.I., Russ. J. Org. Chem., 2003, vol. 39, p. 275.

    Google Scholar 

  10. Kas'yan, A.O., Tarabara, I.N., and Kas'yan, L.I., Russ. J. Org. Chem., 1999, vol. 35, p. 626.

    Google Scholar 

  11. Kasyan, L.I., Tarabara, I.N., Savel'eva, O.A., and Kasyan, A.O., Heteroatom Chem., 2001, vol. 12, p. 119.

    Article  CAS  Google Scholar 

  12. Kas'yan, L.I., Zlenko, O.T., Mamchur, V.I., Kas'yan, A.O., and Tarabara, I.M., Farm. Zh., 2002, no. 2, p. 59; Ukrainian Patent no. 46930, 2002; Byull. no. 6.

  13. Kasyan, L.I., Okovity, S.I., and Kasyan, A.O., Heteroatom Chem., 1997, vol. 8, p. 185.

    CAS  Google Scholar 

  14. Kas'yan, L.I., Tarabara, I.N., Gaponova, R.G, and Kas'yan, A.O., Russ. J. Org. Chem., 1996, vol. 32, p. 1070.

    Google Scholar 

  15. Alder, K., Krieger, H., and Weib, H., Chem. Ber., 1955, vol. 88, p. 144; Alder, K., Heimbach, K., and Reubke, R., Chem. Ber., 1958, vol. 91, p. 1516.

    CAS  Google Scholar 

  16. Wilder, P. and Knight, D.B., J. Org. Chem., 1965, vol. 30, p. 3078; Markov, V.I., Kas'yan, A.O., Tudvaseva, S.P., and Okovityi, S.I., Ukr. Khim. Zh., 1993, vol. 59, p. 575; Markov, V.I., Kas'yan, A.O., and Selyutin, O.B., Ukr. Khim. Zh., 1994, vol. 60, p. 650.

    CAS  Google Scholar 

  17. Nakanishi, K., Infrared Absorption Spectroscopy. Practical, San Francisco: Holden-Day, 1962.

    Google Scholar 

  18. Zefirov, N.S. and Sokolov, V.I., Usp. Khim., 1967, vol. 36, p. 243; Greenberg, A. and Liebman, J., Strained Organic Molecules, New York: Academic, 1978.

    CAS  Google Scholar 

  19. Walborsky, H.M. and Loncrini, D.F., J. Am. Chem. Soc., 1954, vol. 76, p. 5396; Kwart, H. and Vosburgh, W.G., J. Am. Chem. Soc., 1954, vol. 76, p. 5400; Kas'yan, L.I., Russ. J. Org. Chem., 1999, vol. 35, p. 635.

    Article  CAS  Google Scholar 

  20. Tori, K., Kitahonoki, K., Tanida, H., and Tsuyi, T., Tetrahedron Lett., 1964, p. 559; Zefirov, N.S., Kasyan, L.I., Gnedenkov, L.Yu., Shashkov, A.S., and Cherepanova, E.G., Tetrahedron Lett., 1979, p. 949.

  21. Onishchenko, A.S., Dienovyi sintez (Diels-Alder Reaction), Moscow: Akad. Nauk SSSR, 1963.

    Google Scholar 

  22. Shashkov, A.S., Cherepanova, E.G., Kas'yan, L.I., Gnedenkov, L.Yu., and Bombushkar', M.F., Izv. Akad. Nauk SSSR, Ser. Khim., 1980, p. 564.

  23. Savel'eva, O.A., Okovityi, S.I., Kas'yan, A.O., Karpenko, D.V., Tokar', A.V., and Kas'yan, L.I., Vopr. Khim. Khim. Tekhnol., 2004, no. 2, p. 46.

Download references

Author information

Authors and Affiliations

  1. Rhenisch-Westfalische technische Hochschule, Aachen, Germany

    A. O. Kas'yan

  2. Dnepropetrovsk National University, Nauchnyi per. 13, Dnepropetrovsk, 49050, Ukraine

    D. V. Karpenko & L. I. Kas'yan

Authors
  1. A. O. Kas'yan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. V. Karpenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. I. Kas'yan
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 12, 2005, pp. 1802–1809.

Original Russian Text Copyright © 2005 by A. Kas'yan, Karpenko, L. Kas'yan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kas'yan, A.O., Karpenko, D.V. & Kas'yan, L.I. Epoxidation and Heterocyclization of Arenesulfonamides of the Norbornene Series. Russ J Org Chem 41, 1764–1772 (2005). https://doi.org/10.1007/s11178-006-0035-7

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-006-0035-7

Keywords

Search

Navigation