Skip to main content
Log in

Dipole moments, molar Kerr coefficients, and structures of certain substituted bicyclo[2, 2, 2] octenes and their epoxy derivatives

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

Conclusions

  1. 1.

    Dipole moments and molar Kerr coefficients of a number of substituted bicyclo[2, 2, 2]octenes and their epoxy derivatives were measured.

  2. 2.

    The axes of the ellipsoids of polarizability of the carbon-carbon double bond, the oxide and five-membered anhydride rings were calculated.

  3. 3.

    In the oxidation of bicyclooctenes possessing an endo-oriented methyl group or anhydride ring, exo-oxides are formed, while in the oxidation of endo-cyano-derivatives a mixture of exo- and endo-oxides in a 4∶1 ratio is formed.

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. A. N. Vereshchagin and L. A. Grozina, Teoret. i Éksperim. Khimiya,4, 361 (1968).

    Google Scholar 

  2. B. A. Arbuzov, L. A. Grozina, and A. N. Vereshchagin, Teoret. i Éksperim. Khimiya,4, 367 (1968).

    Google Scholar 

  3. K. Alder, K. Heimbach, and R. Reubke, Chem. Ber.,91, 1516 (1958).

    Google Scholar 

  4. A. N. Vereshchagin and B. A. Arbuzov, Izv. Akad. Nauk SSSR, Ser. Khim., 35 (1965).

  5. B. A. Arbuzov, A. N. Vereshchagin, and S. G. Vul'fson, Izv. Akad. Nauk SSSR, Ser. Khim., 155 (1965).

  6. C. G. Lefevre and R. J. W. Lefevre, Rev. Pure Appl. Chem.,5, 261 (1955).

    Google Scholar 

  7. C. G. Lefevre and R. J. W. Lefevre, Physical Methods of Organic Chemistry, A. Weissberger (editor), Vol.1, Part 3, Chapt. 36, New York (1960).

  8. R. J. W. Lefevre, Advances in Physical Organic Chemistry, V. Gold (editor), Vol. 3, London-New York (1965), p. 1.

  9. R. J. W. Lefevre, B. J. Orr, and G. L. D. Ritchie, J. Chem. Soc. (B), 273 (1966).

  10. C. F. Wilcox, J. Amer. Chem. Soc.,82, 414 (1960).

    Google Scholar 

  11. R. J. W. Lefevre, B. J. Orr, and G. L. D. Ritchie, J. Chem. Soc., 3619 (1965).

  12. M. Schwarz and M. M. Maienthal, J. Organ. Chem.,25, 449 (1960).

    Google Scholar 

  13. A. Gagneux and C. A. Grob, Helv. Chim. Acta,42, 2006 (1959).

    Google Scholar 

  14. G. I. Fray, R. J. Hilton, and J. M. Teire, J. Chem. Soc., (C), 592 (1966).

  15. B. Ottar, Acta Chem. Scand.,1, 283 (1947).

    Google Scholar 

  16. V. A. Naumov and V. M. Bezzubov, Zh. Strukt. Khim.,8, 530 (1967).

    Google Scholar 

  17. O. A. Osipov and V. I. Minkin, Handbook of Dipole Moments [in Russian], Vysmaya Shkola (1965).

  18. C. G. Lefevre and R. J. W. Lefevre, J. Chem. Soc., 3549 (1956).

  19. A. N. Vereshchagin and S. G. Vul'fson, Teoret. i. Éksperim. Khimiya,4, 548 (1968).

    Google Scholar 

  20. B. A. Arbuzov, A. N. Vereshchagin, S. G. Vul'fson, and Z. G. Isaeva, Izv. Akad. Nauk SSSR, Ser. Khim., 1966 (1968).

  21. R. Bramley, C. G. Lefevre, R. J. W. Lefevre, and B. P. Rao, J. Chem. Soc., 1183 (1959).

  22. I. L. Fabelinskii, Molecular Refraction of Light [in Russian], Nauka (1965), Appendix 3.

  23. A. S. Onishchenko, Diene Synthesis [in Russian], Izd-vo AN SSSR (1963), p. 42.

  24. K. Kitahonoki, H. Watanabe, and M. Sugiura, Chem. Ber.,95, 2354 (1962).

    Google Scholar 

  25. S. Biagini and M. Cannas, Ricerca Scient., Part 2, Sez. A,8, 1518 (1965).

    Google Scholar 

  26. R. J. W. Lefevre and A. Sundaram, J. Chem. Soc., 4009 (1962).

  27. O. Diels and K. Alder, Liebigs Ann. Chem.,460, 98 (1928).

    Google Scholar 

  28. O. Diels and K. Alder, Chem. Ber.,62, 554 (1929).

    Google Scholar 

  29. B. A. Arbuzov, Z. G. Isaeva, and E. G. Kataev, Uch. Zap. Kazansk. Un-ta,110, No. 9, 175 (1950).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 548–555, March, 1969.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Arbuzov, B.A., Grozina, L.A. & Vereshchagin, A.N. Dipole moments, molar Kerr coefficients, and structures of certain substituted bicyclo[2, 2, 2] octenes and their epoxy derivatives. Russ Chem Bull 18, 489–494 (1969). https://doi.org/10.1007/BF00906963

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00906963

Keywords

Navigation