Skip to main content
Log in

Structural and Kinetic Relations Holding in the Halogen Abstraction from Organohalogen Compounds by Alkyl Radicals

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

Abstract

The relative rate constants were determined, and the absolute rate constants were estimated, for halogen transfer from N,N-dihaloarenesulfonamides, (dichloroiodo)arenes, benzyl bromides, and arenesulfonyl chlorides to cyclohexyl radical and from N,N-dihaloarenesulfonamides to benzyl radical. Polar effect of the substituent was found to be the main factor determining the rate of halogen transfer from benzyl bromides and arenesulfonyl chlorides; it increases with rise in the electrophilicity of the organohalogen substrate due mainly to charge distribution in the transition state.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

REFERENCES

  1. Dneprovskii, A.S. and Eliseenkov, E.V., Zh. Org. Khim., 1988, vol. 24, p. 277.

    CAS  Google Scholar 

  2. Dneprovskii, A.S., Eliseenkov, E.V., and Chulkova, T.G., Russ. J. Org. Chem., 2002, vol. 38, p. 338.

    Article  CAS  Google Scholar 

  3. Davies, A.G., Roberts, B.P., and Smith, J.M., J. Chem. Soc., Perkin Trans. 2, 1972, no. 15, p. 2221.

  4. Hawari, J.A., Davis, S., Engel, P.S., Gilbert, B.C., and Griller, D., J. Am. Chem. Soc., 1985, vol. 107, p. 4721.

    Article  CAS  Google Scholar 

  5. Newcomb, M., Sanchez, R.M., and Kaplan, J., J. Am. Chem. Soc., 1987, vol. 109, p. 1195.

    Article  CAS  Google Scholar 

  6. CRC Handbook of Chemistry and Physics, Lide, D.R., Ed., Boca Raton: CRC, 1999–2000, 80th ed., pp. 9–64.

    Google Scholar 

  7. McMillen, D.F. and Golden, D.M., Ann. Rev. Phys. Chem., 1982, vol. 33, p. 493.

    Article  CAS  Google Scholar 

  8. Neta, N. and Schuler, R.H., J. Phys. Chem., 1973, vol. 77, p. 1368.

    Article  CAS  Google Scholar 

  9. Laarhoven, L.J.J., Born, J.G.P., Arends, I.W.C.E., and Mulder, P., J. Chem. Soc., Perkin Trans. 2, 1997, no. 11, p. 2307.

  10. Silva Correa, C.M.M. and Oliveira, M.A.B.C.S., J. Chem. Soc., Perkin Trans. 2, 1987, no. 6, p. 811.

  11. Fu, Y., Lin, B.-L., Mou, Y., Cheng, Y.-H., and Guo, Q.-X., J. Org. Chem., 2003, vol. 68, p. 4657.

    Article  CAS  PubMed  Google Scholar 

  12. Zavitsas, A.A. and Hanna, G.M., J. Org. Chem., 1975, vol. 40, p. 3782.

    Article  CAS  Google Scholar 

  13. Giese, B. and Meixner, J., Chem. Ber., 1981, vol. 114, p. 2138.

    CAS  Google Scholar 

  14. Dneprovskii, A.S., Kasatochkin, A.N., and Shkurov, V.A., Zh. Org. Khim., 1981, vol. 17, p. 2125.

    CAS  Google Scholar 

  15. Dneprovskii, A.S., Kuznetsov, D.V., Eliseenkov, E.V., Fletcher, B., and Tanko, J.M., J. Org. Chem., 1998, vol. 63, p. 8860.

    Article  CAS  Google Scholar 

  16. Dneprovskii, A.S., Eliseenkov, E.V., and Osmonov, T.A., Russ. J. Org. Chem., 1998, vol. 34, p. 27.

    CAS  Google Scholar 

  17. Giese, B. and Hartung, J., Chem. Ber., 1992, vol. 125, p. 1777.

    CAS  Google Scholar 

  18. Koester, R. and Asmus, K.D., Z. Naturforsch.,Teil B, 1971, vol. 26, p. 1104.

    Google Scholar 

  19. Matyjaszewski, K., Macromolecules, 1998, vol. 31, p. 4710.

    Article  CAS  PubMed  Google Scholar 

  20. Perrin, D.D. and Armarego, W.L.F., Purification of Laboratory Chemicals, Oxford: Pergamon. 1988, 3rd ed., p. 392; Fieser, L.F. and Fieser, M., Reagents for Organic Synthesis, New York: Wiley, 1968, vol. 1.Translated under the title Reagenty dlya organicheskogo sinteza, Moscow: Mir, 1971, vol. 1, p. 34.

    Google Scholar 

  21. Smith, J.E. and Kraus, C.A., J. Am. Chem. Soc., 1951, vol. 73, p. 2751.

    Article  CAS  Google Scholar 

  22. Hartung, J. and Giese, B., Chem. Ber., 1991, vol. 124, p. 387.

    CAS  Google Scholar 

  23. Chattaway, F.D., J. Chem. Soc., 1905, vol. 87, p. 145.

    CAS  Google Scholar 

  24. Organic Syntheses, Horning, E.C., Ed., New York: Wiley, 1966, collect, vol. 3, p. 483.

    Google Scholar 

  25. Cady, G.H., Inorganic Syntheses, Moeller, T., Ed., New York: McGraw-Hill, 1957, vol. 5, p. 156.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 33–39.

Original Russian Text Copyright © 2005 by Dneprovskii, Eliseenkov, Chulkova.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dneprovskii, A.S., Eliseenkov, E.V. & Chulkova, T.G. Structural and Kinetic Relations Holding in the Halogen Abstraction from Organohalogen Compounds by Alkyl Radicals. Russ J Org Chem 41, 28–34 (2005). https://doi.org/10.1007/s11178-005-0115-0

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-005-0115-0

Keywords

Navigation