Abstract
Ionic hydrogenation of 2-perfluoroalkanoylcyclohexane-1,3-diones and their endocyclic enamino derivatives containing a secondary amino group by the action of triethylsilane in trifluoroacetic acid in the presence of a catalytic amount of lithium perchlorate involved regioselective reduction of the side-chain carbonyl group to hydroxy with formation of the corresponding hydroxy diketones and hydroxy amino ketones, respectively. Under analogous conditions endocyclic enamino derivatives possessing a tertiary amino group underwent deacylation to give enamino ketones.
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Khlebnikova, T.S., Isakova, V.G., and Lakhvich, F.A., Dokl. Nats. Akad. Navuk Belarusi, 2007. vol. 51, no. 5, p. 55.
Khlebnikova, T.S., Isakova, V.G., Baranovskii, A.V., and Lakhvich, F.A., Russ. J. Gen. Chem., 2008, vol. 78, no. 10, p. 1954.
Khlebnikova, T.S., Isakova, V.G., and Lakhvich, F.A., Russ. J. Org. Chem., 2009, vol. 45, no. 7, p. 993.
Akhrem, A.A. and Titov, Yu.A., Polnyi sintez steroidov (Total Synthesis of Steroids), Moscow: Nauka, 1967.
Szantay, Cs. and Novak, L., Synthesis of Prostaglandins, Budapest: Academiai Kiado, 1978.
Smith, H., J. Chem. Soc., 1953, no. 3, p. 803.
Kursanov, D.N., Parnes, Z.N., Kalinkin, M.I., and Loim, N.M., Ionnoe gidrirovanie (Ionic Hydrogenation), Moscow: Khimiya, 1979.
Akhrem, A.A., Lakhvich, F.A., Lis, L.G., Khripach, V.A., Fil’chenkov, N.A., Kozinets, V.A., and Pashkovskii, F.S., Dokl. Akad. Nauk SSSR, 1990, vol. 311, no. 6, p. 1381.
Lakhvich, F.A., Lis, L.G., Rubinov, D.B., Rubinova, I.L., and Akhrem, A.A., Zh. Org. Khim., 1989, vol. 25, no. 8, p. 1655.
Lakhvich, F.A., Pashkovskii, F.S., and Lis, L.G., Zh. Org. Khim., 1992, vol. 28, no. 8, p. 1626.
Lakhvich, F.A. and Kozinets, V.A., Russ. J. Org. Chem., 1997, vol. 33, no. 1, p. 42.
Khlebnikova, T.S. and Lakhvich, F.A., Russ. J. Org. Chem., 2000, vol. 36, no. 11, p. 1595.
Schmidt, A. and Boland, W., J. Org. Chem., 2007, vol. 72, no. 6, p. 1699.
Kirsch, P., Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Weinheim: Wiley, 2004.
Khlebnikova, T.S., Isakova, V.G., and Lakhvich, F.A., Russ. J. Gen. Chem., 2008, vol. 78, no. 5, p. 1007.
Khlebnicova, T.S., Isakova, V.G., Baranovsky, A.V., Borisov, E.V., and Lakhvich, F.A., J. Fluorine Chem., 2006, vol. 127, no. 12, p. 1564.
Nitta, M., Soeda, H., and Iino, Y., Bull. Chem. Soc. Jpn., 1990, vol. 63, no. 3, p. 932.
Kondrat’eva, G.V., Gunar, V.I., Ovechkina, L.F., Zav’yalov, S.I., and Krotov, A.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1967, no. 3, p. 633.
Alt, G.H. and Speziale, A.J., J. Org. Chem., 1964, vol. 29, no. 4, p. 794.
Speziale, A.J. and Alt, G.H., US Patent no. 3 288 784; Chem. Abstr., 1967, vol. 66, p. 37 767 u.
Organikum. Organisch-chemisches Grundpraktikum, Berlin: Wissenschaften, 1976, 15th edn. Translated under the title Organikum, Moscow: Mir, 1979, vol. 2, p. 247.
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Original Russian Text © T.S. Khlebnikova, V.G. Isakova, A.V. Baranovskii, F.A. Lakhvich, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 4, pp. 579–586.
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Khlebnikova, T.S., Isakova, V.G., Baranovskii, A.V. et al. Regioselective reduction of 2-perfluoroalkanoylcyclohexane-1,3-diones and their enamino derivatives. Russ J Gen Chem 81, 672–679 (2011). https://doi.org/10.1134/S1070363211040098
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DOI: https://doi.org/10.1134/S1070363211040098