Abstract
Adamantylation of mono-and dinitro-substituted aromatic amines in sulfuric and phosphoric acids and in a mixture of phosphoric and acetic acids gives mainly the corresponding N-adamantyl derivatives. The results of kinetic measurements showed reversible character of the process.
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Khomich, E.V., Kashapov, M.N., Vatsuro, I.M., Shokova, E.A., and Kovalev, V.V., Russ. J. Org. Chem., 2007, vol. 43, no. 2, p. 192.
Shroot, B., Eustache, J., and Bernardon, J.M., Eur. Pat. Appl. no. EP 199 636; Chem. Abstr., 1987, vol. 106, no. 84 197.
Prakash, G.K.S., Yan, P., Török, B., Bucsi, I., Tanaka, M., and Olah, G.A., Catal. Lett., 2003, vol.85, nos. 1–2, p. 1.
Olah, G.A., Török, B., Shamma, T., Török, M., and Prakash, G.K.S., Catal. Lett., 1996, vol. 42, nos. 1–2, p. 5.
Beregszaszi, T., Török, B., Molnar, A., Olah, G.A., and Prakash, G.K.S., Catal. Lett., 1997, vol. 48., nos. 1–2, p. 83.
Bräse, S., Waegell, B., and de Meijere, A., Synthesis, 1998, no. 2, p. 148.
Lednicer, D., Heyd, W.E., Emmert, D.E., TenBrink, R.E., Schurr, P.E., and Day, C.E., J. Med. Chem., 1979, vol. 22, no. 1, p. 69.
Tomaru, A., Kaino, T., Kurihara, T., and Matsumoto, S., JPN Patent Appl. no. 89-124 834, 1989; Chem. Abstr., 1990, vol. 112, no. 45 281.
Tranquillini, M.E. and Finizia, G., PCT Int. Appl. WO 9 425 445; Chem. Abstr., 1995, vol. 122, no. 133 229.
Takeya, Y., JPN Patent no. 93-61 082, 1993; Chem. Abstr., 1993, vol. 119, no. 149 204.
Nicoud, J.F., Mol. Cryst. Liq. Cryst., 1988, vol. 156, p. 257.
Saraev, V.V., Kanakina, T.P., Pevzner, M.S., Golod, E.L., Ugrak, B.I., and Kachala, V.V., Khim. Geterotsikl. Soedin., 1996, no. 8, p. 1078.
Saraev, V.V. and Golod, E.L., Russ. J. Org. Chem., 1997, vol. 33, no. 4, p. 571.
Saraev, V.V., Gavrilov, A.S., and Golod, E.L., Russ. J. Org. Chem., 1999, vol. 35, no. 7, p. 1093.
Gavrilov, A.S., Golod, E.L., Kachala, V.V., and Ugrak, B.I., Russ. J. Org. Chem., 2001, vol. 37, no. 12, p. 1741.
Gavrilov, A.S. and Golod, E.L., Russ. J. Org. Chem., 1999, vol. 35, no. 8, p. 1234.
Eastes, J.W., Aldridge, M.H., and Kamlet, M.J., J. Chem. Soc. B, 1969, no. 8, p. 922.
Tickle, P., Briggs, A.G., and Wilson, J.M., J. Chem. Soc. B, 1970, no. 1, p. 65.
Robinson, R.A., J. Res. NBS, Sec. A, 1967, vol. 71, no. 3, p. 213.
Bolton, P.D. and Hall, F.M., Aust. J. Chem., 1968, vol. 21, no. 4, p. 939.
Bolton, P.D. and Hall, F.M., J. Chem. Soc. B, 1970, no. 7, p. 1247.
Ryabov, R.S., Medvetskaya, I.M., and Vinnik, M.I., Zh. Fiz. Khim., 1966, vol. 40, no. 2, p. 339.
Stetter, H., Weber, J., and Wulff, C., Chem. Ber., 1964, vol. 97, no. 12, p. 3488.
Hammett, L., Physical Organic Chemistry, New York: McGraw-Hill, 1970, 2nd ed.
Tsypin, V.G., Kachala, V.V., Ugrak, B.I., and Golod, E.L., Russ. J. Org. Chem., 2002, vol. 38, no. 1, p. 90.
Geluk, H.W. and Schlatmann, J.L.M.A., Tetrahedron, 1968, vol. 24, no. 15, p. 5361.
Bershtein, I.Ya. and Kaminskii, Yu.L., Spektrofotometricheskii analiz v organicheskoi khimii (Spectrophotometric Analysis in Organic Chemistry), Leningrad: Khimiya, 1975.
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Original Russian Text © S.B. Volkova, O.V. Platonova, V.G. Tsypin, V.A. Polukeev, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 9, pp. 1487–1495.
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Volkova, S.B., Platonova, O.V., Tsypin, V.G. et al. Adamantylation of nitro-substituted aromatic amines in protic acids. Russ J Gen Chem 78, 1719–1727 (2008). https://doi.org/10.1134/S1070363208090132
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DOI: https://doi.org/10.1134/S1070363208090132