Skip to main content
Log in

An ESR spin trap study of polyc hloroalkyl radical rearrangements and conformations

  • Physical Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Rearrangement of ĊH2CCl3 radicals with 1,2-migration of Cl has been studied at temperatures ranging from 25 to −60°C by ESR spin trap methods. ĊH2CCl3 radicals were generated by reacting BrCH2CCl2 with (C2H5)3Si; the unrearranged radicals were identified as spin-adducts with 2-methyl-2-nitroso-3-butanone, and the rearranged ClCH2ĊCl2 radicals as adducts with nitrosodurol.

  2. 2.

    The reaction of (C2H5)3Si withα,α,α-trichloro-ω-bromoalkanes proceeds selectively through detachment of Br and Cl atoms. This same reaction has been studied in other polychloroalkanes.

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

Literature cited

  1. R. G. Gasnov, I. I. Kandror, and R. Kh. Freidlina, Tetrahedron Lett., 1485 (1975).

  2. R. G. Gasanov, I. I. Kandror, M. Ya. Khorlina, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 1758 (1976).

  3. J. Cooper, A. Hudson, and R. A. Jackson, Tetrahedron Lett., 831 (1973).

  4. K. S. Chen, D. Y. H. Tang, L. K. Montgomery, and J. K. Kochi, J. Chem. Soc.,96, 2201 (1974).

    Google Scholar 

  5. S. Terabe, K. Kuruma, and R. Konaka, J. Chem. Soc., Perkin Trans., 2, 1252 (1973).

    Google Scholar 

  6. C. M. Camaggi, R. J. Holman, and M. J. Perkins, J. Chem. Soc., Perkin Trans., 2, 501 (1972).

    Google Scholar 

  7. G. A. Razuvaev, G. A. Abakumov, and V. K. Cherkasov, Dokl. Akad. Nauk SSSR,212, 374 (1973).

    Google Scholar 

  8. R. G. Gasanov and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 2242 (1977).

  9. J. W. Hartgerink, J. B. F. N. Engberts, and Th. J. de Boer, Tetrahedron Lett., 2709 (1971).

  10. R. G. Gasanov, I. I. Kandror, and R. Kh. Freidlina, Dokl. Akad. Nauk SSSR,226, 342 (1975).

    Google Scholar 

  11. C. Lagercrantz, J. Phys. Chem.,75, 3466 (1971).

    Google Scholar 

  12. S. Forshult, C. Lagercrantz, and K. Torssell, Acta Chem. Scand.,23, 522 (1969).

    Google Scholar 

  13. B. A. Énglin, N. A. Grigor'ev, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 1568 (1972).

  14. N. V. Kruglova and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 1028 (1971).

  15. M. Ya. Khorlina, T. T. Vasil'eva, I. A. Shvarts, and V. N. Kost, Izv. Akad. Nauk SSSR, Ser. Khim., 1469 (1971).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii NaukSSSR, Seriya Khimicheskaya, No. 4, pp. 817–821, April, 1978.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gasanov, R.G., Vasil'eva, T.T. & Freidlina, R.K. An ESR spin trap study of polyc hloroalkyl radical rearrangements and conformations. Russ Chem Bull 27, 704–708 (1978). https://doi.org/10.1007/BF00925288

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00925288

Keywords

Navigation