Oxidation With The "o2 - H2o2 - Vauauium Complex - Pyrazine-2-carboxylic Acid" Reagent 9. Oxidation Of Cyclohexene And Decalin

The oxidation of cyclohexene with hydrogen peroxide catalyzed by a vanadium complex and pyrazine-2-carboxylic acid (PCA) in air results in the formation of cyclohex-2-enyl hydroperoxide as the main product and cyclohex-2-enol, cyclohex-2-enone, cyclohex-3-enyl hydroperoxide, cyclohex-3-enol, cyclohexanol, cyclohexane, and 1,2-epoxycyclohexane in lesser amounts. The composition of the products of oxidation of decalin isomers with the system in question is similar to those obtained in the photochemical oxidation with hydrogen peroxide in air and in the oxidation with air in the presence of anthraquinone. A proposed mechanism for the oxidation includes the initiation by hydroxyl radicals generated from hydrogen peroxide under the action of the V - PCA system.472247252Nizova, G.V., Süss-Fink, G., Shul'pin, G.B., (1997) Tetrahedron, 53, p. 3603Shilov, A.E., Shul'pin, G.B., (1995) Aktivatsiya i Kataliticheskie Reaktsii Uglevodorodov [Activation and Catalytic Reactions of Hydrocarbons], , Nauka, Moscow, 400 pp. (in Russian)Shilov, A.E., Shul'pin, G.B., (1997) Chem. Rev., , in pressShul'pin, G.B., Attanasio, D., Suber, L., (1993) Izv. Akad. Nauk, Ser. Khim., p. 64(1993) Russ. Chem. Bull., 42, p. 55. , Engl. TranslShul'pin, G.B., Druzhinina, A.N., Nizova, G.V., (1993) Izv. Akad. Nauk, Ser. Khim., p. 1394(1993) Russ. Chem. Bull., 42, p. 1326. , Engl. TranslNizova, G.V., Shul'pin, G.B., (1994) Izv. Akad. Nauk, Ser. Khim., p. 1212(1994) Russ. Chem. Bull., 43, p. 1146. , Engl. TranslShul'pin, G.B., Süss-Fink, G., (1995) J. Chem. Soc., Perkin Trans., 2, p. 1459Shul'pin, G.B., Drago, R.S., Gonzalez, M., (1996) Izv. Akad. Nauk, Ser. Khim., p. 2514(1996) Russ. Chem. Bull., 45, p. 2386. , Engl. TranslGuerreiro, M.C., Schuchardt, U., Shul'pin, G.B., (1997) Izv. Akad. Nauk, Ser. Khim., p. 780(1997) Russ. Chem. Bull., 46, p. 749. , Engl. TranslShul'pin, G.B., Guerreiro, M.C., Schuchardt, U., (1996) Tetrahedron, 52, p. 13051Shul'pin, G.B., Attanasio, D., Suber, L., (1993) J. Catal., 142, p. 147Shul'pin, G.B., Nizova, G.V., (1992) React. Kinet. Catal. Lett., 48, p. 333Nizova, G.V., Süss-Fink, G., Shul'pin, G.B., (1997) Chem. Commun., p. 397Day, V.W., Klemperer, W.G., Yagasaki, A., (1990) Chem. Lett., p. 1267Baxendale, J.H., Wilson, J.A., (1957) Trans. Faraday Soc., 53, p. 344Rontani, J.-F., Giusti, G., (1990) J. Photochem. Photobiol., A: Chem., 53, p. 69Mimoun, H., Saussine, L., Daire, E., Postel, M., Fischer, J., Weiss, R., (1983) J. Am. Chem. Soc., 105, p. 3101Barton, D.H.R., Hu, B., Li, T., MacKinnon, J., (1996) Tetrahedron Lett., 37, p. 8329Shul'pin, G.B., Druzhinina, A.N., (1992) React. Kinet. Catal. Lett., 47, p. 207Shul'pin, G.B., Nizova, G.V., (1995) Mendeleev Commun., p. 143Shul'pin, G.B., Nizova, G.V., Kozlov, Yu.N., (1996) New J. Chem., 20, p. 1243Barton, D.H.R., Béviére, S.D., Chavasiri, W., Csuhai, E., Doller, D., (1992) Tetrahedron, 48, p. 2895Barton, D.H.R., Béviére, S.D., Chavasiri, W., Csuhai, E., Doller, D., Liu, W.-G., (1992) J. Am. Chem. Soc., 114, p. 2147Bateman, L., Gee, G., (1951) Trans. Faraday Soc., 47, p. 155Russel, G.A., (1957) J. Am. Chem. Soc., 79, p. 3871Mimoun, H., Chaumette, P., Mignard, M., Saussine, L., (1983) Nouv. J. Chim., 7, p. 467Mimoun, H., Mignard, M., Brechot, P., Saussine, L., (1986) J. Am. Chem. Soc., 108, p. 3711Mimoun, H., (1983) Isr. J. Chem., 23, p. 451Butler, A., Clague, M.J., Meister, G.E., (1994) Chem. Rev., 94, p. 625Neumann, R., De La Vega, M., (1993) J. Mol. Cat., 84, p. 93Bonchio, M., Conte, V., Di Furia, F., Modena, G., Moro, S., (1994) J. Org. Chem., 59, p. 626