Electron transfer in reactions of tert-perfluoroalkyl bromides with alkenes and nucleophiles

  • I. N. Rozhkov
  • I. V. Chaplina
Organic Chemistry


Tertiary perfluoroalkyl bromides (RFBr) in nonpolar solvents under mild conditions can be added to the multiple bond of terminal alkenes, alkynes, and butadiene. Slow addition to alkenes at 20°C is accelerated in proton-donating solvents and is catalyzed by readily oxidizable nucleophiles. Bromination of the multiple bond and formation of RFBr reduction products suggests a radicalchain mechanism initiated by electron transfer to the RFBr molecule.


Bromide Electron Transfer Alkene Alkyne Mild Condition 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    B. Evans, I. Weeks, and E. Whitle, J. Chem. Soc. Faraday Trans. 1,79, 1471 (1983).Google Scholar
  2. 2.
    R. N. Haszeldine, J. Fluor. Chem.,33, 307 (1986).Google Scholar
  3. 3.
    I. N. Rozhkov, S. M. Igumnov, S. I. Pletnev, and I. V. Chaplina, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 951 (1990).Google Scholar
  4. 4.
    D. J. Burton and L. J. Kehoe, Tetrahedron Lett.,42, 5165 (1966).Google Scholar
  5. 5.
    C. Wakselman and M. Tordeux, J. Chem. Soc. Chem. Commun.,22, 1701 (1987).Google Scholar
  6. 6.
    Q. Chen, Z. Yang, Ch. Zhao, and Z. Qin, J. Chem. Soc. Perkin Trans, 1, 563 (1988).Google Scholar
  7. 7.
    S. M. Igumnov, I. N. Rozhkov, S. I. Pletnev, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2308 (1989).Google Scholar
  8. 8.
    G. D. Rempel', Yu. A. Borisov, and I. N. Rozhkov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1064 (1990).Google Scholar
  9. 9.
    K. Yoshida, Electrooxidation in Organic Chemistry: The Role of Cation Radicals as Synthetic Intermediates, Wiley-Interscience, New York (1983).Google Scholar
  10. 10.
    I. N. Rozhkov, G. Ya. Bekker, S. M. Igumnov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2222 (1989).Google Scholar
  11. 11.
    L. Eberson, Adv. Phys. Org. Chem.,18, 79 (1982).Google Scholar
  12. 12.
    J. K. Kochi, Angew. Chem. Int. Ed.,27, 1227 (1988).Google Scholar

Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • I. N. Rozhkov
    • 1
  • I. V. Chaplina
    • 1
  1. 1.A. N. Nesmeyanov Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow

Personalised recommendations