Skip to main content
SpringerLink
Log in

Diels-Alder reaction of para-substituted allyl and 2-propynyl benzoates with hexabromo- and tetrabromo-5,5-dimethoxy- 1,3-cyclopentadienes

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

para-Substituted 2-propynyl benzoates are more reactive than the corresponding allyl esters in the Diels-Alder reactions with hexabromo- and tetrabromo-5,5-dimethoxy-1,3-cyclopentadienes. The cycloaddition is favored by the presence of both electron-donor and electron-acceptor substituents in the aromatic ring, in keeping with the “ neutral” reaction scheme. The reactivity of the addends is likely to be determined not only by their donor-acceptor properties but also by the localization energy.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Fukui, K., Acc. Chem. Res., 1971, vol. 4, p. 57.

    Google Scholar 

  2. Herndon, W.S., Chem. Rev., 1972, vol. 72, p. 157.

    Google Scholar 

  3. Houk, K.N., Sims, J., Duke, R.E., Strozier, R.W., and George, J.K., J. Am. Chem. Soc., 1973, vol. 95, p. 7878; Houk, K.N., Sims, J., Watts, C.K., and Luscus, L.J., J. Chem. Soc., 1973, vol. 95, p. 7301; Houk, K.N., Acc. Chem. Res., 1975, vol. 11, p. 361.

    Google Scholar 

  4. Sustman, R., Pure Appl. Chem., 1974, vol. 40, p. 569.

    Google Scholar 

  5. Konovalov, A.I. and Kiselev, V.D., Izv. Ross. Akad. Nauk, Ser. Khim., 2003, no. 2, p. 279.

  6. Sustman, R., Tetrahedron Lett., 1971, vol. 29, p. 2717.

    Google Scholar 

  7. Streitwieser, A., Molecular Orbital Theory for Organic Chemists, New York: Wiley, 1961.

    Google Scholar 

  8. Konovalov, A.I., Zh. Org. Khim., 1969, vol. 5, p. 1713; Konovalov, A.I., Dokl. Akad. Nauk SSSR, 1975, vol. 223, p. 613; Kiselev, V.D., Ustyuchov, A.N., Breus, I.L., et al., Dokl. Akad. Nauk SSSR, 1977, vol. 234, p. 1089.

    Google Scholar 

  9. Briegleb, G., Angew. Chem., Int. Ed. Engl., 1964, vol. 3, p. 617.

    Google Scholar 

  10. Mustafaev, A.M., Adigezalov, N.R., and Kiselev, V.D., Zh. Org. Khim., 1980, vol. 16, p. 2549.

    Google Scholar 

  11. Stull, R.D., Westrum, E.F., Jr., and Sinke, G.C., The Chemical Thermodynamics of Organic Compounds, New York: Wiley, 1969.

    Google Scholar 

  12. Konovalov, A.I., Usp. Khim., 1983, vol. 52, p. 1852; Konovalov, A.I., Solomonov, B.N., and Ustyuchov, A.N., Dokl. Akad. Nauk SSSR, 1973, vol. 213, p. 349.

    Google Scholar 

  13. Mustafaev, A.M., Kasymov, Kh.I., Askerov, G.F., et al., Available from VINITI, 1986, no. 3795-V-86.

  14. Benson, S.W., Thermochemical Kinetics. Methods for Estimation of Thermochemical Data and Rate Parameters, New York: Wiley, 1968.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Baku State University, ul. Z. Khalilova 23, 370148, Baku, Azerbaidjan

    A. M. Magerramov, G. Kh. Velieva, S. D. Murshudova & M. A. Allakhverdiev

  2. Institute of Polymeric Materials, National Academy of Sciences of Azerbaidjan, ul. S. Vurguna 124, 373204, Sumgait, Azerbaidjan

    A. M. Mustafaev

Authors
  1. A. M. Magerramov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. M. Mustafaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. Kh. Velieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. D. Murshudova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. A. Allakhverdiev
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 9, 2004, pp. 1324–1328.

Original Russian Text Copyright © 2004 by Magerramov, Mustafaev, Velieva, Murshudova, Allakhverdiev.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Magerramov, A.M., Mustafaev, A.M., Velieva, G.K. et al. Diels-Alder reaction of para-substituted allyl and 2-propynyl benzoates with hexabromo- and tetrabromo-5,5-dimethoxy- 1,3-cyclopentadienes. Russ J Org Chem 40, 1274–1278 (2004). https://doi.org/10.1007/s11178-005-0004-6

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-005-0004-6

Keywords

Search

Navigation