Radical reaction of methallyl chloride and polychloromethanes withβ-elimination of chlorine atom

  • B. A. Énglin
  • R. D. Ismailov
  • R. Kh. Freidlina
Organic and Biological Chemistry

Conclusions

A study was made of the radical reaction of methallyl chloride with CCl4 and CHCl3 in the presence of peroxide initiators. On the basis of the structures of the isolated products and certain kinetic data a reaction mechanism was proposed with the postulatedβ-elimination of the chlorine atom from the intermediate radicals.

Keywords

Chloride Peroxide Chlorine CHCl3 Reaction Mechanism 

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Literature cited

  1. 1.
    B. A. Énglin, T. A. Onishchenko, V. A. Valovoi, T. A. Babushkina, G. K. Semin, L. G. Zelenskaya, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 332 (1969).Google Scholar
  2. 2.
    B. N. Osipov and B. A. Énglin, Izv. Akad. Nauk SSSR, Ser. Khim., 2430 (1969); B. A. Énglin, V. A. Valovoi, L. G. Zelenskaya, T. A. Babushkina, G. K. Semin, V. B. Bondarev, B. N. Osipov, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 2700 (1970).Google Scholar
  3. 3.
    E. C. Ladd, M. P. Harvey, D. E. Cable, and A. Szayna, US Patent 2,725,411 (1955), Chem. Abstr.,52, 2885d (1958).Google Scholar
  4. 4.
    L. F. Hatch, J. J. Russ, and L. B. Gordon, J. Am. Chem. Soc.,69, 2614 (1947).Google Scholar
  5. 5.
    K. E. Wilzbach, F. R. Mayo, and R. Meter, J. Am. Chem. Soc.,70, 4069 (1948).Google Scholar
  6. 6.
    B. A. Énglin, B. N. Osipov, V. A. Valovoi, T. A. Babushkina, G. K. Semin, V. B. Bondarev, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 1251 (1968).Google Scholar
  7. 7.
    L. J. Bellamy, Infrared Spectra of Complex Molecules [Russian translation], IL (1963), p. 470.Google Scholar
  8. 8.
    J. J. Shipman, V. L. Folt, and S. Krimm, Spectrochim. Acta,18, 1603 (1962).Google Scholar
  9. 9.
    G. K. Semin, Dokl. Akad. Nauk SSSR,158, 1169 (1964).Google Scholar
  10. 10.
    M. S. Kharasch and M. Sage, J. Org. Chem.,14, 79 (1949).Google Scholar
  11. 11.
    B. A. Énglin and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 2097 (1966).Google Scholar
  12. 12.
    R. Kh. Freidlina, Advances in Free Radical Chemistry, G. H. Williams (editor), Academic Press (1965), Vol. 1, p. 211.Google Scholar
  13. 13.
    Cheve Walling, Free Radicals in Solution [Russian translation], IL (1960), pp. 215–217, 242, 256.Google Scholar
  14. 14.
    J. A. Kampmeier, R. P. Geer, A. J. Meskin, and R. M. S'Silva, J. Am. Chem. Soc.,88, 1257 (1966).Google Scholar
  15. 15.
    R. J. Strunk, P. M. DiGiacomo, K. Aso, and H. G. Kuivila, J. Am. Chem. Soc.,92, 2849 (1970).Google Scholar
  16. 16.
    A. Horowitz and L. A. Rajbenbach, J. Am. Chem. Soc.,90, 4105 (1968);91, 4626, 4631 (1969);92, 1634 (1970).Google Scholar
  17. 17.
    A. H. Ewald, S. D. Hamann, and J. E. Stutchbury, Trans. Faraday Soc.,53, 991 (1957); C. Steel, J. Phys. Chem.,64, 1588 (1960); T. L. Dawson, R. D. Lundberg, and F. J. Welch, J. Polymer Sci., A-1,7, 173 (1969).Google Scholar
  18. 18.
    Cheve Walling, Free Radicals in Solution [Russian translation], IL (1960), p. 216.Google Scholar

Copyright information

© Consultants Bureau 1972

Authors and Affiliations

  • B. A. Énglin
    • 1
  • R. D. Ismailov
    • 1
  • R. Kh. Freidlina
    • 1
  1. 1.Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRUSSR

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