Skip to main content
Log in

Steric relations in diene condensations of cyclopentadiene with monosubstituted ethylenes

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

Summary

  1. 1.

    The reactions of cyclopentadiene with vinyl chloride and with vinyl acetate give, in the first place, the kinetically favored endo adducts, which are then converted into their thermodynamically stable isomers.

  2. 2.

    For vinyl chloride the exo adduct is the stable form.

  3. 3.

    11-Bromo-9,10-dihydro-9,10-ethanoanthracene, 9,10-dihydro-9,10-ethanoanthracen-11-ol, and the cyclopentadiene diadduct of vinyl bromide were synthesized.

  4. 4.

    The dipole moments of the compounds synthesized and of some previously described compounds were measured.

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. K. Alder and H. F. Rickert, Ann.,543, 1 (1939).

    Google Scholar 

  2. J. D. Roberts, E. R. Trumball, W. Bennett, and R. Armstrong, J. Amer. Chem. Soc.,72, 3116 (1950).

    Google Scholar 

  3. J. D. Roberts and W. Bennett, J. Amer. Chem. Soc.,76, 4623 (1954).

    Google Scholar 

  4. J. D. Roberts, W. Bennett, and R. Armstrong, J Amer. Chem. Soc.,72, 3329 (1950).

    Google Scholar 

  5. S. J. Cristol, J. R. Douglass, W. C. Firth, and R. E. Krall, J. Organ. Chem.,27, 2711 (1962).

    Google Scholar 

  6. B. A. Arbuzov and A. N. Vereshchagin, Izv. AN SSSR. Ser. khim.,1964, 1004.

  7. K. Alder and G. Stein, Angew. Chem.,50, 510 (1937).

    Google Scholar 

  8. L. Homer and W. Durckheimer, Chem. Ber.,95, 1219 (1962).

    Google Scholar 

  9. Progress in Stereochemistry [Russian translation], edited by W. Klyne and P. de la Mare, (Goskhimizdat, Moscow, 1961), p. 460.

    Google Scholar 

  10. J. Mathieu and A. Halle, Principle of Organic Synthesis [Russian translation], (IL, Moscow, 1962), p. 341.

    Google Scholar 

  11. W. R. Vaugha and K. M. Milton, J. Organ, Chem.,16, 1748 (1951).

    Google Scholar 

  12. K. Alder and G. Stein, Ann.,514, 211 (1934);525, 183 (1936).

    Google Scholar 

  13. O. Achmatowicz, Roczn. Chem.,6, 804 (1926).

    Google Scholar 

  14. J. F. Halverstadt and W. D. Kumler, J. Amer. Chem. Soc.,64, 2988 (1942).

    Google Scholar 

  15. W. D. Kumler, A. Lewis, and I. Meinwald, J. Amer. Chem. Soc.,83, 4591 (1961).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 401–408, March, 1965

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 486–491, March, 1965

Rights and permissions

Reprints and permissions

About this article

Cite this article

Arbuzov, B.A., Vereshchagin, A.N. Steric relations in diene condensations of cyclopentadiene with monosubstituted ethylenes. Russ Chem Bull 14, 466–470 (1965). https://doi.org/10.1007/BF00846604

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00846604

Keywords

Navigation