Abstract
Theoretical and experimental regularities of the regioselectivity of the reduction of one of the two nitro groups in unsymmetrical dinitrobenzenes were studied. It was found that the regioselectivity of the formation of isomeric nitroanilines depends on the structure of the substrate and the nature of the reducing agent. The reduction regioselectivity model was verified, according to which radical anion protonation is the major reaction direction.
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Begunov, R.S., Orlov, V.Yu., Kopeikin, V.V., Kotov, A.D., and Mironov, G.S., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1998, vol. 41, no. 4, p. 61.
Begunov, R.S., Orlov, V.Yu., and Kopeikin, V.V., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1998, vol. 41, no. 5, p. 9.
Bil’kis, I.I. and Shteingarts, V.D., Zh. Org. Khim., 1982, vol. 18, no. 2, p. 359.
Bil’kis, I.I., Uskov, S.I., and Goidin, V.V., Abstracts of Papers, Vsesoyuznaya nauchnaya konferentsiya “Khimiya i tehnologiya organicheskih krasitelei i promezhutochnyh produktov” (Russian Conf. “Chemistry and Technology of Organic Dyes and Intermediate Products”), Leningrad, 1986, p. 73.
Terpko, M.O. and Heck, R.F., J. Org. Chem., 1980, vol. 45, no. 24, p. 4992.
Miesel, J.L., O’Doherty, G.O.P., and Owen, J.M., Catalysis in Organic Synthesis, New York: Academic, 1976.
Bil’kis, I.I., Uskov, S.I., Galdilov, V.S., and Shteingarts, V.D., Zh. Org. Khim., 1986, vol. 22, no. 6, p. 1247.
Bil’kis, I.I., Uskov, S.I., and Shteingarts, V.D., Izv. Akad. Nauk SSSR, Ser. Khim., 1987, no. 3, p. 111.
Bil’kis, I.I., Shteingarts, V.D., Galdilov, V.S., Goidin, V.V., and Uskov, S.I., Zh. Org. Khim., 1991, vol. 27, no. 1, p. 24.
Uskov, S.I., Bil’kis, I.I., and Shteingarts, V.D., Zh. Org. Khim., 1991, vol. 27, no. 1, p. 36.
Barrows, S.E., Cramer, C.J., Truhlar, D.G., Elovitz, M.S., and Weber, E.J., Environ. Sci. Technol., 1996, vol. 30, no. 10, p. 3028.
Houben-Weil, Stuttgart: Thieme, 1957, vol. 11, no. 1, p. 474.
Stern, E.V., Usp. Khim., 1973, vol. 42, no. 2, p. 232.
Kopeikin, V.A., Leibzon, V.N., and Kopeikin, V.V., Abstracts of Papers, Vsesoyuznaya nauchnaya konferentsiya “Khimiya i tehnologiya organicheskih krasitelei i promezhutochnyh produktov” (Russian Conf. “Chemistry and Technology of Organic Dyes and Intermediate Products”), Leningrad, 1988, p. 29.
Wen-Kan Xing and Ogata, Y., J. Org. Chem., 1983, vol. 48, no. 15, p. 2515.
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Original Russian Text © V.Yu. Orlov, R.S. Begunov, N.Yu. Demidova, A.I. Rusakov, 2006, published in Zhurnal Obshchei Khimii, 2006, Vol. 76, No. 1, pp. 81–86.
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Orlov, V.Y., Begunov, R.S., Demidova, N.Y. et al. Effect of the electronic structure of the radical anions of 4-substituted 1,2-and 1,3-dinitrobenzenes on the regioselectivity of reduction of the nitro groups. Russ J Gen Chem 76, 76–81 (2006). https://doi.org/10.1134/S1070363206010154
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DOI: https://doi.org/10.1134/S1070363206010154