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.
Similar content being viewed by others
References
Woodward, R.B. and Baer, H., J. Am. Chem. Soc., 1948, vol. 70, p. 1161.
Weis, C.D., J. Org. Chem., 1962, vol. 27, p. 3520.
Brion, F., Tetrahedron Lett., 1982, vol. 23, p. 5299.
Fringuelli, F. and Taticchi, A., Dienes in the Diels—Alder Reaction, New York: Wiley, 1990.
Kappe, C.O., Murphree, S., and Padwa, A., Tetrahedron, 1997, vol. 53, p. 14179.
Shipman, M., Contemp. Org. Synth., 1995, vol. 2, p. 1.
Marchionni, C., Vogel, P., and Roversi, P., Tetrahedron Lett., 1996, vol. 37, p. 4149.
Woo, S. and Keay, B., Synthesis, 1996, p. 669.
Lautens, M., Synlett, 1993, p. 177.
Lautens, M., Chiu, P., Ma, S., and Rovis, T., J. Am. Chem. Soc., 1995, vol. 117, p. 532.
Lautens, M. and Klute, W., Angew. Chem., Int. Ed. Engl., 1996, vol. 35, p. 442.
Cooley, J.H. and Williams, R.V., J. Chem. Educ., 1997, vol. 74, p. 582.
Riddick, J.A., Bunger, W.B., and Sakano, T.K., Organic Solvents: Physical Properties and Methods of Purification, New York: Wiley, 1986, 4th ed.
Kornilov, D.A. and Kiselev, V.D., Int. J. Chem. Kinet., 2015, vol. 47, p. 389.
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.
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.
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.
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.
Kiselev, V.D., Kornilov, D.A., and Konovalov, A.I., Int. J. Chem. Kinet., 2017, vol. 49, p. 562.
Kiselev, V.D., Kornilov, D.A., Lekomtseva, I.I, and Konovalov, A.I., Int. J. Chem. Kinet., 2015, vol. 47, p. 289.
Kiselev, V.D. and Konovalov, A.I., J. Phys. Org. Chem., 2009, vol. 22, p. 466.
Kiselev, V.D., Kornilov, D.A., Sedov, I.A., and Konovalov, A.I., Int. J. Chem. Kinet., 2017, vol. 49, p. 61.
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.
Sauer, J., Wiest, H., and Mielert, A., Ber., 1964, vol. 97, p. 3183.
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.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Full Member of the Russian Academy of Sciences A.I. Konovalov on his 85th anniversary
Rights and permissions
About this article
Cite this article
Kornilov, D.A., Kiselev, V.D., Anikin, O.V. et al. High Pressure, Temperature, and Solvent Effects on the Rate of the Diels-Alder Reaction of Furan with N-Phenylmaleimide. Russ J Org Chem 55, 7–10 (2019). https://doi.org/10.1134/S1070428019010020
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428019010020