Abstract
[4+2]-Codimerization of cyclohexa-1,3-diene, cyclopentadiene, and their methyl-substituted derivatives in the presence of H-forms of synthetic mordenite and natural clinoptilolite was studied. Application of zeolites as catalyst decreases the rate of di- and trimerization of cyclopentadiene and its methyl-substituted derivatives, increases the reaction selectivity with respect to their codimers with cyclohexa-1,3-diene and its methylsubstituted derivatives as well as 4-vinylcyclohexene. Epoxidation of the synthesized codimers with the adduct of hydrogen peroxide with urea in the presence of gadolinium- and neodymium-containing phosphorus molybdenum complexes as catalysts has been investigated, and optimal conditions for preparation of diepoxides of tricyclic dienes have been found.
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Berents, A.D., Vol-Einshtein, A.B., Mukhina, T.I., and Avrekh, G.L., Pererabotka zhidkikh produktov piroliza (Recycling of Liquid Pyrolysis Products), Moscow: Khimiya, 1985.
Jeong, J.-P., Lee, O.-S., and Yang, K., Bull. Korean Chem. Soc., 2002, vol. 23, no. 6, p. 829.
Marton, A., Parvulescu, H., Draghici, C., Varga, R.A., and Gheorgyhin, M.D., Tetrahedron, 2009, no. 65, p. 7504. DOI: 10.1016/j.tet.2009.07.02
The Diels-Alder Reaction: Selected Practical Methods, Fringuelli, F. and Taticchi, A., Eds., John Wiley & Sons, 2002. DOI: 10.1002/0470845813.ch7.
Sarotti, A.M., Pisano, P.L., and Pellegrinet, S.C., Org. Biomol. Chem., 2010, no. 8, p. 5069. DOI: 10.1039/c0ob00020e.
Palko, M., Sohar, P., and Fülöp, F., Molecules, 2011, no. 16, p. 7691. DOI: 10.3390/molecules16097691.
Alimardanov, Kh.M., Sadygov, O.A., Garibov, N.I., and Abdullaeva, M.Ya., Russ. J. Org. Chem., 2012, vol. 48, no. 10, p. 1302. DOI: 10.1134/S1070428012100077
Kuznetsova, L.I., Kuznetsova, N.I., Lisitsyn, A.S., Bekk, I.E., Likholobov, V.A., and Ansel’, Zh.E., Kinet. Catal., 2007, vol. 48, no. 1, p. 38. DOI: 10.1134/S0023158407010065.
Carman, R.M. and Rayner, A.C., Austr. J. Chem., 1994, vol. 47, no. 2, p. 195. DOI: 10.1071/CH9940195.
Salomatina, O.V., Yarovaya, O.I., and Barkhash, V.A., Russ. J. Org. Chem., 2005, vol. 41, no. 2, p. 155 DOI: 10.1007/s11178-005-0141-y.
Kera, Y., Inagaki, A., Mochizuki, Y., Kominami, H., Yamaguchi, Sh., and Ichihara, J., J. Mol. Catal. A, 2002, vol. 184, nos. 1–2, p. 413. DOI: 10.1016/S1381-1169 (02)00028-6.
Timofeeva, M.N., Pai, Z.P., Tolstikov, A.G., Kustova, G.N., Selivanova, N.V., Berdnikova, P.V., Brylyakov, K.P., Shangina, A.B., and Utkin, V.A., Russ. Chem. Bull., 2003, vol. 52, no. 2, p. 480. DOI: 10.1023/A:1023495824378.
Modern Heterogeneous Oxidation Catalysis Design Reactions and Characterization, Mizuno, N., Ed., Weinheim: Wiley-VCH Verlag, 2009.
Neumann, R., Inorg. Chem., 2010, vol. 49, no. 8, p. 3594. DOI: 10.1021/ic9015383.
Aref’ev, O.A., Vorob’eva, N.S., Epishev, V.I., and Petrov, Al.A., Neftekhim., 1972, vol. 12, no. 2, p. 171
Onishchenko, A.S., Dienovyi sintez (Diene Synthesis), Moscow: Akad. Nauk SSSR, 1963.
Alimardanov, H.M., Sadygov, O.A., Babaev, R.S., and Abdullaeva, M.Y., Process of Petrochem. and Oil Refining, 2006, no. 2 (25), p. 17
Zefirov, N.S. and Sokolov, V.I., Russ. Chem. Rev., 1967, vol. 36, no. 2, p. 87.
Kas’yan, L.I., Okovityi, S.I., Bomushkar’, M.F., and Driuk, V.G., Russ. J. Org. Chem., 2000, vol. 36, no. 2, p. 195.
Mirkin, L.I., Spravochnik po rentgenostrukturnomu analizu polikristallov (Handbook of X-Ray Analysis of Polycrystalline), Moscow: Fizmatgiz, 1961
ASTM-Powder Diffraction File published by the “JCPDS,” International Center for Diffraction Data 1977, USA.
Paken, A.M., Epoksidnye soedineniya i epoksidnye smoly (Epoxy Compounds and Epoxy Resins), Leningrad: Goskhimizdat. 1962
Musaev, M.R., Alimardanov, Kh.M., and Makhmudzhova, G.T., Author’s Certificate no. 1133253, 1984; Bull. Izobret., 1985, no. 1.
Dobroserdova, N.B. and Amisimov, A.V., Praktikum po neftekhimicheskomu sintezu (Workshop on Petrochemical Synthesis), Mosocw: Mosk. Gos. Univ., 1981.
Bellami, L.J., Infrared Spectra of Complex Molecules, New York: Wiley, 1960.
Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley & Sons, 1972.
Ionin, B.I. and Ershov, B.A., NMR Spectroscopy in Organic Chemistry, Leningrad: Khimiya, 1967.
Alimardanov, Kh.M., Sadygov, O.A., Hajiyev, T.A., Abdullaeva, M.Y., Asirova, R.B., and Babaev, N.R., Process of Petrochem. and Oil Refining, 2007, no. 5, p. 57.
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Original Russian Text © N.I. Garibov, Kh.M. Alimardanov, N.R. Dadashova, O.A. Sadygov, M.B. Almardanova, A.D. Kuliev, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 5, pp. 726–734.
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Garibov, N.I., Alimardanov, K.M., Dadashova, N.R. et al. Epoxidation of the products of codimerization of cyclopentadiene and cyclohexadiene hydrocarbons catalyzed by lanthanide-molybdenum polyoxometalates. Russ J Gen Chem 85, 1025–1033 (2015). https://doi.org/10.1134/S1070363215050035
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DOI: https://doi.org/10.1134/S1070363215050035