Advertisement

Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Stereodirection of the radical telomerization of propylene by carbon tetrachloride

Conclusions

  1. 1.

    The influence of temperature (55–200°) on the distribution of racemic diastereomeric i-, s-, and h-modifications of 1, 1, 1, 7-tetrachloro-3, 5-dimethyloctane in the radical telomerization of propylene with CCl4 was studied in a broad range of reagent concentrations.

  2. 2.

    Using statistical methods of evaluating the relative content of i-, s-, and h-forms, the possibility of stereodirected chain transfer and addition at the double bond of CCl3[CH2CH(CH3)]n radicals was demonstrated (chiefly the syndio-direction, although the yield of the i-form almost doubles from 55 to 200°); the stereochemical nature of the substitution with the participation of aliphatic radicals was studied for the first time.

  3. 3.

    A hypothesis was advanced on the stereoregulating influence of the substituent in the penultimate unit of the growing telomer radical (1, 3-asymmetrical induction).

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

Literature cited

  1. 1.

    B. A. Bohm and P. I. Abell, Chem. Revs.,62, 599 (1962); É. Iliel, Stereochemistry of Carbon Compounds [Russian translation], Mir (1965, pp. 347, 369.

  2. 2.

    D. I. Davies and S. J. Cristol, in: Advances in Free Radical Chem., Vol. 1, G. H. Williams (editor), Academic Press (1965), p. 155.

  3. 3.

    P. Boldt and L. Schulz, Tetrahedron Letters, 4351 (1967); C. L. Osborn, T. V. van Auken, and D. J. Trecker, J. Amer. Chem. Soc.,90, 5806 (1968).

  4. 4.

    L. A. Singer and N. P. Kong, Tetrahedron Letters, 643 (1967); J. Amer. Chem. Soc.,89, 5251, 6805 (1967).

  5. 5.

    F. D. Greene, G. Chu, and J. Walia, J. Amer. Chem. Soc.,84, 2463 (1962); J. Organ. Chem.,29, 1285 (1964).

  6. 6.

    S. J. Cristol, L. K. Gaston, and T. Tiedeman, J. Organ. Chem.,29, 1279 (1964).

  7. 7.

    F. R. Jensen, L. H. Gale, and J. E. Rodgers, J. Amer. Chem. Soc.,90, 5793 (1968).

  8. 8.

    F. A. Bovey and G. V. D. Tiers, Fortschr. Hochpolymer Forsch.,3, 139 (1963).

  9. 9.

    U. Johnsen, Kolloid-Z. Polymere,210, 1 (1966); R. C. Ferguson, Rubber Chem. and Technol.,40, 385 (1967); H. Y. Chen, ibid.,41, 47 (1967).

  10. 10.

    Y. Kato and A. Nishioka, J. Chem. Soc. Japan,68, 1461 (1965); K. Yokoto and Y. Ishii, ibid.,68, 1473 (1965); K. Matsuzaki, A. Ishida, N. Tateno, T. Asakura, H. Hasegawa, and K. Tameda, ibid.,68, 852 (1965); Y. Iwakura, F. Toda, T. Ito, and K. Aoshima, Makromolek. Chem.,104, 26 (1967); K. Matsuzaki, A. Ishida, and N. Tateno, J. Polymer Sci.,C16, 2111 (1967).

  11. 11.

    H. Yuki, K. Hatada, Y. Kikuchi, and T. Niinomi, J. Polymer Sci.,B6, 753 (1968).

  12. 12.

    K. Matsuzaki, T. Uryu, A. Ishida, T. Ohki, and M. Takeuchi, J. Polymer Sci.,A-1, 5, 2167 (1967).

  13. 13.

    C. E. Bawn, W. H. Janes, and A. M. North, J. Polymer Sci.,C4, 427 (1963).

  14. 14.

    C. L. Arcus, J. Chem. Soc., 2801 (1955).

  15. 15.

    J. W. L. Fordham, G. H. McCain, and L. E. Alexander, J. Polymer Sci.,39, 335 (1959).

  16. 16.

    S. Brownstein, S. Bywater, and D. J. Worsfold, Makromolek. Chem.,48, 127 (1961); J. Phys. Chem.,66, 2067 (1962).

  17. 17.

    G. M. Burnett, F. L. Ross, and J. N. Hay, Makromolek. Chem.,105, 1 (1967).

  18. 18.

    K. C. Ramey and N. D. Field, J. Polymer Sci.,B3, 63, 69 (1965)

  19. 19.

    F. A. Bovey, F. P. Hood, E. W. Anderson, and L. C. Snyder, J. Chem. Phys.,42, 3900 (1965); M. Murano and R. Yamadera, J. Polymer Sci.,B5, 333 (1967); F. A. Bovey, F. P. Hood, E. W. Anderson, and K. L.Kornegay, J. Phys. Chem.,71, 312 (1967).

  20. 20.

    L. L. Ferstanding and F. C. Goodrich, J. Polymer Sci.,43, 373 (1960).

  21. 21.

    R.Kh. Freidlina, B. N. Osipov, and B. A. Énglin, Izv. Akad. Nauk SSSR, Ser. Khim. (1970), in press.

  22. 22.

    R. D. Spencer, M. B. Fulton, and B. H. Beggs, Polymer Preprints, Amer. Chem. Soc., Div. Polymer Chem.,1, 126 (1960).

  23. 23.

    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).

  24. 24.

    E. N. Zil'berman, L. M. Bobinova, and V. L. Zvezdin, Zh. Obshch. Khim.,3, 2151 (1967).

  25. 25.

    B. A. Énglin, B. N. Osipov, and R.Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 1736, 2223 (1967).

  26. 26.

    D. Braun, M. Herner, U. Johnsen, and W. Kern, Makromolek Chem.,51, 15 (1962).

  27. 27.

    R. Chujo, J. Phys. Soc. Japan,21, 2669 (1966).

  28. 28.

    W. Cooper, in: Stereochemistry of Macromolecules, Vol. 2, A. D. Ketley (editor), Dekker, New York (1967), p. 219.

  29. 29.

    T. J. Leitereg and D. J. Cram, J. Amer. Chem. Soc.,90, 4011, 4019 (1968).

  30. 30.

    S. Sykora, Collect. Czechoslov. Chem. Commun.,33, 3514 (1968); P. E. McMahon, Trans. Faraday Soc.,61, 197 (1965); T. Fujiwara and T. Shimanouchi, J. Chem. Phys.,39, 1138 (1963); Y. Fujiwara and S. Fujiwara, Bull. Chem. Soc. Japan,37, 1005 (1964); D. Doskocilova, J. Stokr, B. Schneider, H. Pivcova, M. Kolinsky, J. Petranek, and D. Lim, J. Polymer Sci.,C16, 215 (1967).

Download references

Author information

Additional information

The article is published on the basis of a resolution of the Conference of Editors-in-Chief of the Journals of the Academy of Sciences of the USSR from July 12, 1962, as the dissertation work of B.N. Osipov.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskya, No. 11, pp. 2430–2438, November, 1969.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Osipov, B.N., Énglin, B.A. Stereodirection of the radical telomerization of propylene by carbon tetrachloride. Russ Chem Bull 18, 2276–2282 (1969). https://doi.org/10.1007/BF00906494

Download citation

Keywords

  • Propylene
  • Statistical Method
  • Double Bond
  • CCl4
  • Tetrachloride