Skip to main content
Log in

Effect of pressure on the rate of the Diels-Alder reaction of diethyl azodicarboxylate with 9,10-dimethylanthracene

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

Abstract

The enthalpy, entropy, and volume of activation and volume of the Diels-Alder reaction of diethyl azodicarboxylate with 9,10-dimethylanthracene in 1,2-dichloroethane have been determined. Possible factors responsible for the sharp difference between the volumes of activation and reaction are considered.

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

References

  1. Mitsunobu, O. and Yamada, Y., Bull. Chem. Soc. Jpn., 1967, vol. 40, p. 2380.

    Article  CAS  Google Scholar 

  2. Diels, O. and Alder, K., Justus Liebigs Ann. Chem., 1926, vol. 450, p. 237.

    Article  CAS  Google Scholar 

  3. Paquette, L.A., Encyclopedia of Reagents for Organic Synthesis, Chichester: Wiley, 1995, p. 1790.

    Google Scholar 

  4. Rodgman, A. and Wright, G.F., J. Org. Chem., 1953, vol. 18, p. 465.

    Article  CAS  Google Scholar 

  5. Wurche, F. and Klärner, F.-G., High Pressure Chemistry, van Eldik, R. and Klärner, F.-G., Eds., Weineim: Wiley-VCH, 2002, p. 77.

  6. Jenner, G. and Salem, R.B., J. Chem. Soc., Perkin Trans. 2, 1990, p. 1961.

    Google Scholar 

  7. Sauer, J., Wiest, H., and Mielert, A., Chem. Ber., 1964, vol. 97, p. 3183.

    Article  CAS  Google Scholar 

  8. Konovalov, A.I. and Kiselev, V.D., Zh. Org. Khim., 1986, vol. 22, p. 1133

    CAS  Google Scholar 

  9. Konovalov, A.I., Breus, I.P., Sharagin, I.A., and Kiselev, V.D., Zh. Org. Khim., 1979, vol. 15, p. 361.

    CAS  Google Scholar 

  10. Kiselev, V.D., Shakirova, I.I., Kornilov, D.A., Kashaeva, H.A., Potapova, L.N., and Konovalov, A.I., J. Phys. Org. Chem., 2013, vol. 26, p. 47.

    Article  CAS  Google Scholar 

  11. Sauer, J., Wiest, H., and Mielert, A., Z. Naturforsch., Teil B, 1962, vol. 17, p. 203.

    Google Scholar 

  12. Koerner von Gustorf, E., White, D.V., Kim, B., Hess, D., and Leitich, J., J. Org. Chem., 1970, vol. 35, p. 1155.

    Article  CAS  Google Scholar 

  13. Franzus, B. and Surridge, J., J. Org. Chem., 1962, vol. 27, p. 1951.

    Article  CAS  Google Scholar 

  14. Kiselev, V.D., Int. J. Chem. Kinet., 2013, vol. 45, p. 613.

    Article  CAS  Google Scholar 

  15. Kiselev, V.D., Bolotov, A.V., Satonin, A.P., Shakirova, I.I., Kashaeva, E.A., and Konovalov, A.I., J. Phys. Chem. B, 2008, vol. 112, p. 6674.

    Article  CAS  Google Scholar 

  16. Kinart, W.J. and Kinart, C.M., Phys. Chem. Liq., 2003, vol. 14, p. 173.

    Article  Google Scholar 

  17. Burrage, M.E., Cookson, R.C., Gupte, S.S., and Stevens, I.D.R., J. Chem. Soc., Perkin Trans. 2, 1975, p. 1325.

    Google Scholar 

  18. Armarego, W.L.F. and Chai, C.L.L., Purification of Laboratory Chemicals, Amsterdam: Elsevier, 2009, 6th ed., p. 124.

    Google Scholar 

  19. Sintezy organicheskikh soedinenii (Syntheses of Organic Compounds), Nesmeyanov, A.N. and Bobrov, P.A., Eds., Moscow: Akad. Nauk SSSR, 1950, vol. 1, p. 54.

    Google Scholar 

  20. Riddick, J.A., Bunger, W.B., and Sakano, T.K., Organic Solvents. Physical Properties and Methods of Purification, New York: Wiley, 1986, 4th ed.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. D. Kiselev.

Additional information

Original Russian Text © V.D. Kiselev, D.A. Kornilov, E.A. Kashaeva, L.N. Potapova, A.I. Konovalov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 4, pp. 503–506.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kiselev, V.D., Kornilov, D.A., Kashaeva, E.A. et al. Effect of pressure on the rate of the Diels-Alder reaction of diethyl azodicarboxylate with 9,10-dimethylanthracene. Russ J Org Chem 50, 489–493 (2014). https://doi.org/10.1134/S1070428014040071

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428014040071

Keywords

Navigation