Skip to main content
SpringerLink
Log in

Fluorination of Bi- and polycyclic aromatic hydrocarbons with N-fluorobis(phenylsulfonyl)amine in the absence of solvent

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

Abstract

Reactions of N-fluorobis(phenylsulfonyl)amine with naphthalene, 1-methylnaphthalene, phenanthrene, anthracene, and pyrene without solvent were investigated. Sometimes the fluorination of aromatic compounds with N-fluorobis(phenylsulfonyl)amine without solvent proceeded more selectively than at the use of fluorinating reagents in solution.

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. Hiyama, T., Organofluorine Compounds, Berlin: Springer, 2000.

    Google Scholar 

  2. Kirsch, P., Modern Fluoroorganic Chemistry. Synthesis Reactivity Applications. Weinheim: Wiley-VCH, 2004.

    Google Scholar 

  3. Uneyama, K., Organofluorine Chemistry. Oxford: Blackwell, Publ., 2006, p. 3.

    Book  Google Scholar 

  4. Taylor, S.D., Kotoris, C.C., and Hum, G., Tetrahedron, 1999, vol. 55, p. 12431.

    Article  CAS  Google Scholar 

  5. Furin, G.G. and Fainzil’berg, A.A., Usp. Khim., 1999, vol. 68, p. 725.

    Google Scholar 

  6. Furin, G.G., Houben-Weyl, Meth. Org. Chem. Stuttgart: Thieme, 2000, vol. E10, p. 432.

    Google Scholar 

  7. Gouverneur, V. and Greedy, B., Chem. Eur. J., 2002, vol. 8, p. 767.

    Article  Google Scholar 

  8. Dawood, K.M., Tetrahedron, 2004, vol. 60, p. 1435.

    Article  CAS  Google Scholar 

  9. Singh, R.P. and Shreeve, J.M., Acc. Chem. Res., 2004, vol. 37, p. 31.

    Article  CAS  Google Scholar 

  10. Ibrahim, H. and Togni, A., Chem. Commun., 2004, p. 1147.

  11. Salvatore, R., Chem. Today, 2004, vol. 22, p. 57.

    Google Scholar 

  12. Nyffeler, P.T., Durón, S.G., Burkart, M.D., Vincent, S.P., and Wong, C.-H., Angew. Chem., Int. Ed., 2005, vol. 44, p. 192.

    Article  CAS  Google Scholar 

  13. Umemoto, T., Advances in Organic Synthesis. Modern Organo-fluorine Chemistry — Synthetic Aspects, Atta-ur-Rahman, Laali, K.K., Eds, Bentham, Sci. Publ., 2006, vol. 2, p. 159.

  14. Stavber, S. and Zupan, M., Adv. Org. Synth. Modern, Organofluorine, Chemistry — Synthetic Aspects, Atta-ur-Rahman, Laali, K.K., Eds, Bentham, Sci. Publ., 2006, vol. 2, p. 213.

  15. Okazaki, T. and Laali, K.K., Advances in Organic Synthesis. Modern Organo-fluorine Chemistry — Synthetic Aspects, Atta-ur-Rahman, Laali, K.K., Eds, Bentham, Sci. Publ., 2006, vol. 2, p. 353.

  16. Ma, J.-A. and Cahard, D., Chem. Rev., 2008, vol. 108, no. 9, PR1.

    Article  Google Scholar 

  17. Pravst, I., Zupan, M., and Stavber, S., Curr. Org. Chem., 2009, vol. 13, p. 47.

    Article  CAS  Google Scholar 

  18. Differding, E. and Ofner, H., Synlett., 1991, p. 187.

  19. Laali, K.K. and Borodkin, G.I., J. Chem. Soc., Perkin Trans. II, 2002, p. 953.

  20. Borodkin, G.I., Zaikin, P.A., and Shubin, V.G., Tetrahedron Lett., 2006, vol. 47, p. 2639.

    Article  CAS  Google Scholar 

  21. Heravi, M.R.P., J. Fluor. Chem., 2008, vol. 129, 217.

    Article  CAS  Google Scholar 

  22. Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Zh. Org. Khim., 2009, vol. 45, p. 1483.

    Google Scholar 

  23. Loupy, A., Modern Solvents in Organic Synthesis, Knochel, P., Ed., Berlin: Springer, 1999, p. 153.

    Chapter  Google Scholar 

  24. Pavlinac, J., Zupan, M., and Stavber, S., J. Org. Chem., 2006, vol. 71, p. 1027; Iskra, J., Zupan, M., and Stavber, S., Org. Biomol. Chem., 2003, p. 1528.

    Article  CAS  Google Scholar 

  25. Eaborn, C., Golborn, P., Spillett, R.E., and Taylor, R., J. Chem. Soc. B., 1968, p. 1112.

  26. Singh, S., DesMarteau, D.D., Zuberi, S.S., Witz, M., and Huang, H.-N., J. Am. Chem. Soc., 1987, vol. 109, p. 7194.

    Article  CAS  Google Scholar 

  27. Zupan, M., Iskra, J., and Stavber, S., J. Fluor. Chem., 1995, vol. 70, p. 7.

    Article  CAS  Google Scholar 

  28. Shamma, T., Buchholz, H., Prakash, G.K.S., and Olah, G.A., Israel, J. Chem., 1999, vol. 39, p. 207.

    CAS  Google Scholar 

  29. Appelman, E.H., Basile, L.J., and Hayatsu, R., Tetrahedron, 1984, vol. 40, p. 189.

    Article  CAS  Google Scholar 

  30. Stavber, S. and Zupan, M., J. Fluor. Chem., 1981, vol. 17, p. 597.

    Article  CAS  Google Scholar 

  31. Anand, S.P., Quarterman, L.A., Christian, P.A., Hyman, H.H., and Filler, R., J. Org. Chem., 1975, vol. 40, p. 3796.

    Article  CAS  Google Scholar 

  32. Agranat, I., Rabinovitz, M., Selig, H., and Lin, C.-H., Chem. Lett., 1975, p. 1271.

  33. Zupan, M. and Pollak, A., J. Org. Chem., 1975, vol. 40, p. 3794.

    Article  CAS  Google Scholar 

  34. Selig, H., Rabinovitz, M., Agranat, I., Lin, C.-H., and Ebert, L., J. Am. Chem. Soc., 1976, vol. 98, p. 1601.

    Article  CAS  Google Scholar 

  35. Laali, K.K., Tanaka, M., Forohar, F., Cheng, M., and Fetzer, J.C., J. Fluor. Chem., 1998, vol. 91, p. 185.

    Article  CAS  Google Scholar 

  36. Chung, Y., Duerr, B.F., McKelvey, T.A., Nanjappan, P., and Czarnik, A.W., J. Org. Chem., 1989, vol. 54, p. 1018.

    Article  CAS  Google Scholar 

  37. Stavber, S. and Zupan, M., Chem. Lett., 1996, p. 1077.

  38. Rabinovitz, M., Agranat, I., Selig, H., and Lin, C.-H., J. Fluor. Chem., 1977, vol. 10, p. 159.

    Article  CAS  Google Scholar 

  39. Dolbier, W.R., Keaffaber, J.J., Burkholder, C.R., Koroniak, H., and Pradhan, J., Tetrahedron., 1992, vol. 48, p. 9649.

    Article  CAS  Google Scholar 

  40. Lutnaes, B.F., Luthe, G., Brinkman, U.A.T., Johansen, J.E., and Krane, J., Magn. Res. Chem., 2005, vol. 43, p. 588.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090, Russia

    G. I. Borodkin, I. R. Elanov & V. G. Shubin

Authors
  1. G. I. Borodkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. R. Elanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. G. Shubin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. I. Borodkin.

Additional information

Original Russian Text © G.I. Borodkin, I.R. Elanov, V.G. Shubin, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 9, pp. 1318–1323.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Borodkin, G.I., Elanov, I.R. & Shubin, V.G. Fluorination of Bi- and polycyclic aromatic hydrocarbons with N-fluorobis(phenylsulfonyl)amine in the absence of solvent. Russ J Org Chem 46, 1317–1322 (2010). https://doi.org/10.1134/S1070428010090095

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428010090095

Keywords

Search

Navigation