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Russian Journal of Organic Chemistry

, Volume 55, Issue 1, pp 7–10 | Cite as

High Pressure, Temperature, and Solvent Effects on the Rate of the Diels-Alder Reaction of Furan with N-Phenylmaleimide

  • D. A. Kornilov
  • V. D. KiselevEmail author
  • O. V. Anikin
  • A. O. Kolesnikova
  • A. A. Shulyat’ev
Article
  • 3 Downloads

Abstract

The effects of temperature, solvent nature, and high pressure on the rate of the Diels-Alder reaction of furan with N-phenylmaleimide were studied. A weak acceleration of the title reaction in proton-donor media was observed in comparison to other cycloaddition and ene reactions. The volumes of activation and reaction coincided within the experimental error, in keeping with the presumed cyclic transition state.

Keywords

high hydrostatic pressure Diels-Alder reaction N-phenylmaleimide furan volume of activation volume of reaction 

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References

  1. 1.
    Woodward, R.B. and Baer, H., J. Am. Chem. Soc., 1948, vol. 70, p. 1161.CrossRefGoogle Scholar
  2. 2.
    Weis, C.D., J. Org. Chem., 1962, vol. 27, p. 3520.CrossRefGoogle Scholar
  3. 3.
    Brion, F., Tetrahedron Lett., 1982, vol. 23, p. 5299.CrossRefGoogle Scholar
  4. 4.
    Fringuelli, F. and Taticchi, A., Dienes in the Diels—Alder Reaction, New York: Wiley, 1990.Google Scholar
  5. 5.
    Kappe, C.O., Murphree, S., and Padwa, A., Tetrahedron, 1997, vol. 53, p. 14179.CrossRefGoogle Scholar
  6. 6.
    Shipman, M., Contemp. Org. Synth., 1995, vol. 2, p. 1.CrossRefGoogle Scholar
  7. 7.
    Marchionni, C., Vogel, P., and Roversi, P., Tetrahedron Lett., 1996, vol. 37, p. 4149.CrossRefGoogle Scholar
  8. 8.
    Woo, S. and Keay, B., Synthesis, 1996, p. 669.Google Scholar
  9. 9.
    Lautens, M., Synlett, 1993, p. 177.Google Scholar
  10. 10.
    Lautens, M., Chiu, P., Ma, S., and Rovis, T., J. Am. Chem. Soc., 1995, vol. 117, p. 532.CrossRefGoogle Scholar
  11. 11.
    Lautens, M. and Klute, W., Angew. Chem., Int. Ed. Engl., 1996, vol. 35, p. 442.CrossRefGoogle Scholar
  12. 12.
    Cooley, J.H. and Williams, R.V., J. Chem. Educ., 1997, vol. 74, p. 582.CrossRefGoogle Scholar
  13. 13.
    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
  14. 14.
    Kornilov, D.A. and Kiselev, V.D., Int. J. Chem. Kinet., 2015, vol. 47, p. 389.CrossRefGoogle Scholar
  15. 15.
    Kiselev, V.D., Bolotov, A.V., Satonin, A.P., Shakirova, I.I., Kashaeva, H.A., and Konovalov, A.I., J. Phys. Chem. B, 2008, vol. 112, p. 6674.CrossRefGoogle Scholar
  16. 16.
    Kiselev, V.D., Kornilov, D.A., Anikin, O.V., Plemenkov, V.V., and Konovalov, A.I., Russ. J. Org. Chem., 2018, vol. 54, p. 1080.CrossRefGoogle Scholar
  17. 17.
    Kiselev, V.D., Kornilov, D.A., Anikin, O.V., Shulyatiev, A.A., Kolesnikova, A.O., and Konovalov, A.I., Int. J. Chem. Kinet., 2018, vol. 50, p. 651.CrossRefGoogle Scholar
  18. 18.
    Kiselev, V.D., Kornilov, D.A., Anikin, O.V., Sedov, I.A., and Konovalov, A.I., Russ. J. Org. Chem., 2017, vol. 53, p. 1864.CrossRefGoogle Scholar
  19. 19.
    Kiselev, V.D., Kornilov, D.A., and Konovalov, A.I., Int. J. Chem. Kinet., 2017, vol. 49, p. 562.CrossRefGoogle Scholar
  20. 20.
    Kiselev, V.D., Kornilov, D.A., Lekomtseva, I.I, and Konovalov, A.I., Int. J. Chem. Kinet., 2015, vol. 47, p. 289.CrossRefGoogle Scholar
  21. 21.
    Kiselev, V.D. and Konovalov, A.I., J. Phys. Org. Chem., 2009, vol. 22, p. 466.CrossRefGoogle Scholar
  22. 22.
    Kiselev, V.D., Kornilov, D.A., Sedov, I.A., and Konovalov, A.I., Int. J. Chem. Kinet., 2017, vol. 49, p. 61.CrossRefGoogle Scholar
  23. 23.
    Kiselev, V.D., Kornilov, D.A., Anikin, O.V., Latypova, L.I., and Konovalov, A.I., Russ. J. Phys. Chem. A, 2017, vol. 91, p. 464.CrossRefGoogle Scholar
  24. 24.
    Sauer, J., Wiest, H., and Mielert, A., Ber., 1964, vol. 97, p. 3183.Google Scholar
  25. 25.
    Zhulin, V.M., Kel’tseva, M.V., Bogdanov, V.S., Koreshkov, Yu.D., and Kabotyanskaya, E.B., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, vol. 39, p. 456.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • D. A. Kornilov
    • 1
  • V. D. Kiselev
    • 1
    Email author
  • O. V. Anikin
    • 1
  • A. O. Kolesnikova
    • 1
  • A. A. Shulyat’ev
    • 1
  1. 1.Butlerov Institute of ChemistryKazan (Volga Region) Federal UniversityKazan, TatarstanRussia

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