Abstract
The catalytic effect of AlCl3 on the Diels-Alder reaction of 9,10-dimethylanthracene with maleic anhydride is dramatically weakened on addition of a competing n donor, dibutyl ether. The n,v complex of aluminum chloride with dibutyl ether is considerably more stable than the complex with maleic anhydride; therefore, the catalytic effect is suppressed even at comparable concentrations of these n donors.
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REFERENCES
Woodward, R.B. and Hoffmann, R., The Concentration of Orbital Symmetry, Weinheim: Chenie, 1970.
Kiselev, V.D. and Konovalov, A.I., Usp. Khim., 1989, vol. 58, no. 3, pp. 383-416.
Scharf, H.D., Plum, H., Fleischhauer, J., and Schleker, W., Chem. Ber., 1979, vol. 112, no. 3, pp. 862-882.
Sustmann, R., Bohm, M., and Sauer, J., Chem. Ber., 1979, vol. 112, no. 3, pp. 883-889.
Gur'yanova, E.N., Gol'dshtein, I.P., and Romm, I.P., Donorno-aktseptornaya svyaz' (Donor—Acceptor Bond), Moscow: Khimiya, 1973.
Kiselev, V.D., Shakirov, I.M., and Konovalov, A.I., Zh. Org. Khim., 1984, vol. 20, no. 7, pp. 1454-1459.
Kiselev, V.D., Shakirov, I.M., and Konovalov, A.I., Zh. Org. Khim., 1986, vol. 22, no. 5, pp. 1034-1045.
Kiselev, V.D., Mavrin, G.V., and Konovalov, A.I., Zh. Org. Khim., 1982, vol. 18, no. 12, pp. 2505-2509.
Gol'dshtein, I.P., Gur'yanova, E.N., and Shcherbakova, E.S., Zh. Obshch. Khim., 1970, vol. 40, no. 2, pp. 183-188.
Kiselev, V.D., Shakirov, I.M., and Konovalov, A.I., Zh. Org. Khim., 1985, vol. 21, no. 6, pp. 1215-1221.
Sintezy organicheskikh soedinenii (Syntheses of Organic Compounds), Moscow: Akad. Nauk SSSR, 1950, coll. 1, p. 54.
Weissberger, A. and Proskauer, E.S., Organic Solvents. Physical Properties and Methods of Purification, Riddick, J.A. and Toops, E.E., Eds., New York: Interscience, 1955.
Kiselev, V.D., Kashaeva, E.A., Luzanova, N.A., and Konovalov, A.I., Thermochim. Acta, 1997, vol. 303, no. 2, pp. 225-228.
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Kiselev, V.D., Kashaeva, E.A. & Konovalov, A.I. Effect of a Competing n Donor on the Rate of AlCl3-Catalyzed Diels-Alder Reaction of 9,10-Dimethylanthracene with Maleic Anhydride. Russian Journal of General Chemistry 72, 1793–1796 (2002). https://doi.org/10.1023/A:1023305732611
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DOI: https://doi.org/10.1023/A:1023305732611