Abstract
Analysis was performed of reduction processes of epoxy derivatives obtained from unsaturated compounds belonging to various groups: alkenes, cycloalkenes, spiroalkanes, and substituted norbornenes. The regio- and stereochemistry was discussed of reactions between epoxides and complex metal hydrides, of catalytic hydrogenation, and some other processes. The mechanisms were considered of the reduction reactions, in particular, those involving radical and ion radical intermediates.
Similar content being viewed by others
References
Otero-Lobato, M.J., Kaats-Richrers, V.E.M., Koper, C., Vlietstra, E.J., Havenith, R.W.A., Jenneskens, L.W., and Seinen, W., Mutations Res., 2005, vol. 581, p. 115.
Dryuk, V.G., Kartsev, V.G., and Voitsekhovskaya, M.A., Oksirany — sintez i biologicheskaya aktivnost’ (Oxiranes: Synthesis and Biological Activity), Moscow: Bogorodskii Pechatnik, 1999, 527 p.
Baertschi, S.W., Rancy, K.D., Stone, M.P., and Harris, T.M., J. Am. Chem. Soc., 1998, vol. 110, p. 7929.
Smith, G.I., Synthesis, 1984, p. 629.
Armagero, W.E., Stereochemistry of Heterocyclic Compounds. Part II. Oxygen Heterocycles, New York: Interscience, Willey & Sons, 1977.
Bonini, C. and Righi, G., Synthesis, 1994, p. 225.
Gansдuer, A., Barchuk, A., and Fielenbach, D., Synthesis, 2004, p. 2567.
Ranu, B.C., Synlett., 1993, p. 885.
Oishi, T. and Nakata, T., Synthesis, 1990, p. 635.
Winterfeldt, E., Synthesis, 1975, p. 617.
Kas’yan, L.I., Zh. Org. Khim., 1999, vol. 35, p. 661.
Kas’yan, L.I., Kas’yan, A.O., and Tarabara, I.N., Zh. Org. Khim., 2001, vol. 37, p. 1430.
Kas’yan, A.O., Kas’yan, L.I., Okovityi, S.I., and Tarabara, I.N., Alitsiklicheskie epoksidnye soedineniya. Reaktsionnaya sposobnost’ (Alicyclic Epoxy Compounds. Reactivity), Dnepropetrovsk: Izd. Dnepropetrovsk. Natsional. Iniv., 2003, 515 p.
Petragnani, N. and Comasseto, J.V., Synthesis, 1986, p. 1.
Chen, S.-C., Synthesis, 1974, p. 691.
Hodgson, D.M. and Gras, E., Synthesis, 2000, p. 1625.
Ivanov, D., Vassilev, G., and Panayotov, I., Synthesis, 1975, p. 83.
Rajan, Babu, T.V., and Nugent, W.A., J. Am. Chem. Soc., 1994, vol. 114, p. 986.
Bonini, C., Fabio, R., Sotgiu, G., and Cavagnero, S., Tetrahedron, 1989, vol. 45, p. 2895.
Brown, H.C. and Krishnamurthy, S., Tetrahedron, 1979, vol. 35, p. 567.
Hardouin, C., Chevallier, F., Rousseau, B., and Doris, E., J. Org. Chem., 2001, vol. 66, p. 1046.
Gansauer, A., Synlett., 1998, p. 801.
Boyd, D.R., Sharma, N.D., Agarwal, S.K., Gadaginamath, G.S., O’Kane, G.A., Jennings, W.B., Yagi, H., and Jerina, D.M., J. Chem. Soc., Perkin Trans. I, 1993, p. 424.
Hasegawa, E., Chiba, N., Nakajima, A., Suzuki, K., Yoneoka, A., and Iwaya, K., Synthesis, 2001, p. 1248.
Brown, H.C., Harasimhan, S., and Somayaji, V., J. Org. Chem., 1983, vol. 48, p. 3091.
Kozina, M.P., Timofeeva, L.P., Luk’yanova, V.A., Pimenova, S.M., and Kas’yan, L.I., Zh. Fiz. Khim., 1988, vol. 17, p. 1203.
Liebmann, J.F. and Greenberg, A., Chem. Rew., 1989, vol. 89, p. 1225.
Kas’yan, L.I., Gorb, L.G., Seferova, M.F., Chernousov, D.M., Svyatkin, V.A., and Boldeskul, I.E., Zh. Org. Khim., 1990, vol. 26, p. 3.
Kas’yan, L.I., Seferova, M.F., and Porubleva, L.V., Zh. Org. Khim., 1992, vol. 28, p. 449.
Kas’yan, L.I. and Seferova, M.F., Visnik Dnipropetrovs’kogo Univ, Khimiya, 2002, no. 7, p. 30.
Michailovic, M.L., Andrejevic, V., Milovanovic, J., and Jancovic, J., Helv. Chim. Acta, 1976, vol. 59, p. 2305.
Michailovic, M.L., Andrejevic, V., Jancovic, J., and Mihailovic, M.L., Glasnik Khem. Drusht. Beograd., 1978, vol. 43, p. 83.
Andrejevic, V., Bjelacovic, M., Michailovic, M.M., and Mihailovic, M.L., Helv. Chim. Acta, 1985, vol. 68, p. 2030.
Posner, G.H. and Rogers, D.L., J. Am. Chem. Soc., 1979, vol. 99, p. 8208.
Ciaccio, J.A., Addess, K.J., and Bell, T.W., Tetrahedron Lett., 1986, vol. 27, p. 3697.
Ford, G.P. and Smith, C.T., J. Am. Chem. Soc., 1987, vol. 109, p. 1325.
Jacober, S.P. and Hanzlic, R.P., J. Am. Chem. Soc., 1986, vol. 108, p. 1594.
Okovityi, S.I. and Kas’yan, L.I., Visnik Dnipropetrovs’kogo Univ., Khimiya, 2002, no. 7, p. 6.
Sundararaman, P., Barth, G., and Djerassi, C., J. Am. Chem. Soc., 1981, vol. 103, p. 5004.
Solladie-Covallo, A., Lupattelli, P., Marsol, C., Isarno, T., Bonini, C., Caruso, L., and Maiorella, A., Eur., J. Org. Chem., 2002, p. 1439.
Chini, M., Crotti, P., Flippin, L.A., and Macchia, F., J. Org. Chem., 1990, vol. 55, p. 4265.
Chini, M., Crotti, P., Flippin, L.A., Macchia, F., and Pineschi, M., J. Org. Chem., 1992, vol. 57, p. 1405.
Chini, M., Crotti, P., Gardelli, C., and Macchia, F., J. Org. Chem., 1994, vol. 59, p. 4131.
Crotti, P., Di, Bussolo, V., Favero, L., Macchia, F., and Pineschi, M., Eur., J. Org. Chem., 1998, p. 1675.
Gramain, J.-C., Mavel, S., Troin, Y., and Vallee-Coyet, D., Tetrahedron, 1991, vol. 47, p. 7287.
Schwab, J.M., J. Org. Chem., 1983, vol. 48, p. 2105.
Flaherty, T.M. and Gervay, J., Tetrahedron Lett., 1996, vol. 37, p. 961.
Andrejevic, V., Bjelakovic, M., and Mihailovic, M., J. Serb. Chem. Soc., 1987, vol. 52, p. 685.
Gurudutt, K.N. and Ravindranath, B., Synthesis, 1983, p. 888.
Toromanoff, E., Tetrahedron, 1981, vol. 37, p. 3141.
Vedejs, E. and Gapinski, D.M., J. Am. Chem. Soc., 1983, vol. 105, p. 5058.
Avila, D., Davies, A.G., and Davison, J.G.E., J. Chem. Soc., Perkin Trans. II, 1988, p. 1847.
Sonawane, H.R., Bellur, N.S., Kulkarni, D.G., and Ahaja, J.R., Synlett., 1993, p. 875.
Mori, K., Nakayama, T., and Takikawa, H., Tetrahedron Lett., 1996, vol. 37, p. 3741.
Brimble, M.A., Jonston, A.D., and Furneaux, R.H., J. Org. Chem., 1998, vol. 63, p. 471.
Vankar, Y.D., Chaudhuri, N.C., and Rao, C.T., Tetrahedron Lett., 1987, 28 vol., p. 551.
Richer, J.-C., Poirier, M.-A., Maroni, Y., and Manuel, S. Canad., J. Chem., 1980, no. 1, p. 39.
Sorochinskaya, E.I. and Kozhin, S.A., Zh. Obshch. Khim., 1975, vol. 45, p. 2537.
Lange, J.H.M., Sommerdijk, N.A.J.M., Dols, P.P.M.A., Arnouts, E.G., Klunder, A.J.H., and Zwanenburg, B., Tetrahedron Lett., 1991, vol. 32, p. 3127.
Klunder, A.J.H., Zwanenburg, B., and Liu, Z.-Y., Tetrahedron Lett., 1991, vol. 32, p. 3131.
Liu, Z.-Y. and Chu, X.-J., J. Chem. Soc., Perkin Trans. I, 1993, p. 2155.
Katagari, N., Matsuhashi, Y., Kokofuda, H., Takebayashi, M., and Kaneko, C., Tetrahedron Lett., 1997, vol. 38, p. 1961.
Gadikota, R.R., Callam, C.S., and Lowary, T.L., J. Org. Chem., 2001, vol. 66, p. 9046.
Malinovskii, M.S., Kas’yan, L.I., Ovsyanik, V.D., and Ivchenko, O.V., Zh. Org. Khim., 1973, vol. 9, p. 2077.
Kas’yan, L.I., Zefirov, N.S., Gnedenkov, L.Yu., Stepanova, N.V., Shashkov, A.S., and Cherepanova, E.G., Zh. Org. Khim., 1982, vol. 18, p. 1212.
Kasyan, L.I., Okovity, S.I., and Kasyan, A.O., Heteroatom Chem., 1997, vol. 8, p. 185.
Kasyan, L.I., Tarabara, I.N., Savel’yeva, O.A., and Kasyan, A.O., Heteroatom Chem., 2001, vol. 12, p. 119.
Kas’yan, L.I., Tarabara, I.N., Savel’eva, O.A., and Kas’yan, A.O., Zh. Org. Khim., 1997, vol. 33, p. 1429.
Gray, A.P. and Heitmeier, D.R., J. Org. Chem., 1969, vol. 34, p. 3253.
Kas’yan, L.I., Krishchik, O.V., Kas’yan, A.O., and Tarabara, I.N., Zh. Org. Khim., 2004, vol. 40, p. 1878.
Gabioud, R., Chapuis, G., and Vogel, P., J. Org. Chem., 1982, vol. 47, p. 3316.
Sugita, K., Onaka, M., and Izumi, Y., Tetrahedron Lett., 1990, vol. 31, p. 7467.
Soai, E., Ookawa, A., Oyamada, H., and Taskase, M., Heterocycles, 1982, vol. 19, p. 1371.
Nukui, S., Sodeoka, M., Sasai, H., and Shibasaki, M., J. Org. Chem., 1995, vol. 60, p. 398.
Onaka, M., Sugita, K., and Imuzi, Y., J. Chem. Soc. Jpn. Chem. and Ind. Chem., 1989, p. 588.
Yoon, N.M. and Kim, K.E., J. Org. Chem., 1987, vol. 52, p. 5564.
Chakraborty, T.K. and Tapadar, S., Tetrahedron Lett., 2001, vol. 42, p. 1375.
Collins, C.J., Fisher, G.B., Reem, A., Goralski, C.T., and Singaram, D.B., Tetrahedron Lett., 1997, vol. 38, p. 529.
Brown, H.C., Kim, S.C., and Krishnamurthy, S., J. Org. Chem., 1980, vol. 45, p. 1.
Kawasaki, M., Matsuda, F., and Terashima, S., Tetrahedron Lett., 1988, vol. 29, p. 791.
McWhorter, S.E. and Schore, N.E., J. Org. Chem., 1991, vol. 56, p. 338.
Nishigama, S., Ikeda, Y., Yoshida, S., and Yamamura, S., Tetrahedron Lett., 1989, vol. 30, p. 105.
Ookawa, A., Kitade, M., and Soai, K., Heterocycles, 1988, vol. 27, p. 213.
Ookawa, A., Hiratsuka, H., and Soai, K., Bull. Chem. Soc. Jpn., 1987, vol. 60, p. 1813.
Rotella, D.P., Tetrahedron Lett., 1989, vol. 30, p. 1913.
Santaniello, E., Ferraboschi, P., Fiecchi, A., Crisenti, P., and Manzocchi, A., J. Org. Chem., 1987, vol. 52, p. 671.
Alcaide, B., Areces, P., Borredon, E., Biurrun, C., Castells, J.P., and Plumet, J., Heterocycles, 1990, vol. 31, p. 1997.
Dresler, R. and Uzarewicz, A., Polish J. Chem., 2000, vol. 74, p. 1581.
Yanada, K., Yanada, R., and Meguri, H., Chem. Pharm. Bull., 1989, vol. 37, p. 3423.
Hu, Y., Uno, M., Harada, A., and Takahashi, S., Chem. Lett., 1990, p. 797.
Hu, Y., Uno, M., Harada, A., and Takahashi, S., Bull. Chem. Soc. Jpn., 1991, vol. 64, p. 1884.
Lynas-Cray, J.I. and Stirling, C.J.M., Rec. Trav. Chim., 1986, vol. 105, p. 341.
Santosh, L.G.R. and Iyengar, D.S., Synth. Commun., 1997, vol. 27, p. 1731.
Finkielztein, L.M., Aguirre, J.M., Lantano, B., Alesso, E.N., and Iglesias, G.Y.M., Synth. Commun., 2004, vol. 34, p. 895.
Grison, C., Coutrot, F., Comoy, C., Lemilbeau, C., and Coutrot, P., Tetrahedron Lett., 2000, vol. 41, p. 6571.
Lalancette, J.M., Freche, A., Brindle, J.R., and Laliberte, M., Synthesis, 1972, p. 526.
Ranu, B.C. and Das, A.R., J. Chem. Soc. Chem. Commun., 1990, p. 1334.
Sreekumar, R., Padmakumar, R., and Rugmini, P., Tetrahedron Lett., 1998, vol. 39, p. 5151.
Zaidlewicz, M., Uzarewicz, A., and Sarnowski, R., Synthesis, 1979, p. 62.
Golikov, A.G., Kriven’ko, A.P., and Reshetov, P.V., Khimiya i biologicheskaya aktivnost’ sinteticheskikh i prirodnykh soedinenii (Chemistry and Biological Activity of Synthetic and Natural Compounds), Moscow: ICSPF, 2006, vol. 1, p. 65.
Le Drian, C. and Vogel, P., Helv. Chim. Acta, 1987, vol. 70, p. 1703.
Le Drian, C. and Vogel, P., Helv. Chim. Acta, 1988, vol. 71, p. 1399.
Fuji, H., Oshima, K., and Utimoto, K., Chem. Lett., 1992, p. 697.
Kawakami, T., Shibata, I., Baba, A., and Matsuda, H., J. Org. Chem., 1993, vol. 58, p. 7608.
Dominquez, B.M. and Cullis, P.M., Tetrahedron Lett., 1999, vol. 40, p. 5783.
EPV Zayavka 1146031, 2001; Ref. Zh. Khim., god02.03-19N82P.
USSR Inventor’s Certificate 1657483, 1991; Ref. Zh. Khim., 1992, 2N60P.
Bartok, M. and Notheisz, F., J. Chem. Soc. Chem. Commun., 1980, p. 667.
Gareia, J.G., Voll, R.J., and Younathan, E.S., Tetrahedron Lett., 1991, vol. 32, p. 5273.
Ishiyama, J., Yashima, H., Matsuo, H., Senda, Y., Smaizumi, S., Hanaya, K., and Muramutsu, T., Chem. Lett., 1989, p. 989.
Accrombessi, G.C., Geneste, P., and Olive, J.-L., J. Org. Chem., 1980, vol. 45, p. 4139.
Mitsui, S., Sugi, Y., Fujimoto, M., and Yokoo, K., Tetrahedron, 1974, vol. 30, p. 31.
Accrombessi, G., Geneste, P., Olive, J.-L., and Pavia, A.A., Tetrahedron, 1981, vol. 37, p. 3135.
Chan, A.S. and Coleman, J.P., J. Chem. Soc. Chem. Commun., 1991, p. 535.
Kuhn, T., Tamm, C., Riesen, A., and Zehnder, M., Tetrahedron Lett., 1989, vol. 10, p. 693.
Schobert, R. and Hohlein, U., Synlett., 1990, p. 465.
Parrish, J.D. and Little, R.D., Org. Lett., 2002, vol. 4, p. 1439.
Fernandez-Mateos, A., Nava, E.M., Coca, G.P., Silvo, A.R., and Gonzales, R.R., Org. Lett., 1999, vol. 1, p. 607.
Barrero, A.F., Oltra, J.E., Cuerva, J.M., and Rosales, A., The 12th European Symp. Organic Chemistry, Groningen., 2001, p. 2.
Gansдuer, A., Pierobon, M., and Bluhm, H., Angew Chem., Int. Ed., 1998, vol. 37, p. 101.
Naemann, W.R., Synthesis, 1987, p. 665.
Morphy, J.A. and Patterson, C.W., J. Chem. Soc., Perkin Trans. I, 1993, p. 405.
Dickinson, J.M., Murphy, J.A., Patterson, C., and Wooster, N.F., J. Chem. Soc., Perkin Trans. I, 1990, p. 1179.
Frimer, A.A., Afri, M., Baumel, S.D., Gilinsky-Sharon, P., Rosenthal, Z., and Gottlieb, H.E., J. Org. Chem., 2000, vol. 65, p. 1807.
Bonini, C., Fabio, R.D., Tetrahedron Lett., 1988, vol. 29, p. 819.
Kim, S., Koh, J.S., J. Chem. Soc. Chem. Commun., 1992, p. 1377.
Afzal, M., Nalton, J.C., J. Chem. Soc., Perkin Trans. II, 1999, p. 937.
Kim, S. and Lee, S., Tetrahedron Lett., 1991, vol. 32, p. 6575.
Kim, S., Lee, S., and Koh, J.S., J. Am. Chem. Soc., 1991, vol. 113, p. 5706.
Rawal, V.H., Newton, R.C., and Krishnamurthy, V., J. Org. Chem., 1990, vol. 55, p. 5181.
Kakimoto, Y.-I., Ogasawara, Y., Nishida, A., Kawahara, N., Nishida, M., and Takayanagi, H., Tetrahedron, 2000, vol. 56, p. 7173.
Robertson, J., Pillai, J., and Lush, R.K., Chem. Soc. Rew., 2001, vol. 30, p. 94.
Baguley, P.A. and Walton, J.C., Angew Chem., Int. Ed., 1998, vol. 37, p. 3073.
Lund, T. and Lund, H., Tetrahedron Lett., 1986, vol. 27, p. 95.
Kasai, P.H., J. Am. Chem. Soc., 1990, vol. 112, p. 4313.
Epling, G.A. and Wang, Q., J. Chem. Soc. Chem. Commun., 1992, p. 1133.
Cossy, J., Aclinou, P., Bellosta, V., Furet, N., Baranne-Lafont, J., Sparfel, D., and Soachaud, C., Tetrahedron Lett., 1991, vol. 32, p. 1315.
Dorigo, A.E., Houk, K.N., and Cohen, T., J. Am. Chem. Soc., 1989, vol. 111, p. 8976.
Gleiter, R., Herb, T., and Lange, H., J. Org. Chem., 1996, vol. 61, p. 9236.
Gurudutt, K.N., Rao, S., and Sharo, A.K., Indian J. Chem. B, 1991, vol. 30, p. 345.
Cohen, T., Jeong, I.-H., Mudryk, B., Bhupathy, M., and Awad, M.M.A., J. Org. Chem., 1990, vol. 55, p. 1528.
Tkachev, A.V., Zh. Org. Khim., 1990, vol. 26, p. 1706.
Benkeser, R.A., Rappa, A., and Wolsieffer, L.A., J. Org. Chem., 1986, vol. 51, p. 3391.
Karaman, R. and Fry, J.L., Tetrahedron Lett., 1989, vol. 30, p. 4931.
Fort, Y., Vanderesse, R., and Caubere, P., Tetrahedron Lett., 1985, vol. 26, p. 3111.
Miyashita, M., Suzuki, T., and Yoshikoshi, A., Tetrahedron Lett., 1987, vol. 28, p. 4293.
Takano, S., Moriya, M., and Ogasawara, K., Synlett., 1993, p. 601.
Miyashita, M., Suzuki, T., and Yoshikoshi, A., Tetrahedron Lett., 1989, vol. 30, p. 1819.
Miyashita, M., Hoshino, M., Suzuki, T., and Yoshikoshi, A., Chem. Lett., 1988, p. 507.
De, la, Pradilla, R.F., Alhambra, C., Castellanos, A., Fernandez, J., Manzano, P., Montero, C., Urena, M., and Viso, A., J. Org. Chem., 2005, vol. 70, p. 10693.
Concellon, J.M., Bardales, E., and Llavona, R., J. Org. Chem., 2003, vol. 68, p. 1585.
Inokuschi, T., Kusumoto, M., and Torii, S., J. Org. Chem., 1990, vol. 55, p. 1548.
Choi, J.H., Lee, S.J., Joo, C.R., Kim, J.S., and Baek, D.J., Bull. Korean Chem. Soc., 1999, vol. 20, p. 1384.
Torii, S., Okumoto, H., Nakayasu, S., and Kotani, T., Chem. Lett., 1989, p. 1975.
Aldous, D.J., Dalencon, A.J., and Steel, P.G., Org. Lett., 2002, vol. 4, p. 1159.
Tsuji, J. and Mandai, T., Synthesis, 1996, p. 1.
Noguchi, Y., Yamada, T., Uchiro, H., and Kobayashi, S., Tetrahedron Lett., 2000, vol. 41, p. 7493.
David, H., Dupuis, L., Guillerez, M., and Guile, F., Tetrahedron Lett., 2000, vol. 41, p. 3335.
Nagasawa, K., Shimizu, I., and Nakata, T., Tetrahedron Lett., 1996, vol. 37, p. 6881.
Yudin, A.K., Aziridines and Epoxides in Organic Synthesis, Weinheim: Wiley-VCH, 2006, 492 p.
Marson, C.M., Walker, A.J., Pickering, J., Hobson, A.D., Wrigglesworth, R., and Edge, S.J., J. Org. Chem., 1993, vol. 58, p. 5944.
Shimazaki, M., Hara, H., Suzuki, K., and Tsuchihashi, G., Tetrahedron Lett., 1987, vol. 28, p. 5891.
Tu, Y.A., Fan, C.A., Ren, S.R., and Chan, A.S.C., J. Chem. Soc., Perkin Trans. I, 2000, p. 3791.
Klinot, J., Liska, J., Forgacova, A., Budesinsky, M., Protiva, J., Hilgard, S., and Vystreil, A., Coll. Czech. Chem. Commun., 1989, vol. 54, p. 413.
Tu, Y.-Q., Sun, L.-D., and Wang, P.-Z., J. Org. Chem., 1999, vol. 64, p. 629.
Tu, Y.-Q., Xia, W.-J., Wang, P.-Z., Zhai, J.-J., and Chen, Y.-Z., Chem., J. Chin. Univ., 1999, vol. 20, p. 587.
Tu, Y.-Q., Yang, L.-M., and Chen, Y.-Z., Chem. Lett., 1998, p. 285.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © L.I. Kas’yan, A.O. Kas’yan, E.A. Golodaeva, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 2, pp. 167–194.
Kas’yan Liliya Ivanovna was born in the town Staryi Oskol, Belgorod Oblast’. She graduated from Odessa State University in 1960. Candidate of Chemical Sciences since 1970, Doctor of Chemical Sciences since 1990. Honored Worker of Science and Engineering of the Ukraine. Professor at the Chair of Organic Chemistry at the Dnepropetrovsk National University.
Field of scientific interests: chemistry of epoxy compounds, chemistry of cage-like compounds, mechanisms and stereochemistry of organic reactions.
Kas’yan Andrei Olegovich was born in 1966 in Dnepropetrovsk. In 1988 he graduated from Dnepropetrovsk State University. Candi-date of Chemical Sciences since 1993. In 1996–2002 worked in Universities of Halle and Aachen (Germany). At present he is the Head of Laboratory at the ProBioGen Co (Berlin).
Field of scientific interests: chemistry of cage-like compounds.
Golodaeva Elena Anatol’evna was born in 1977 in Sverdlovsk. In 1999 she graduated from Dnepropetrovsk State University. Candidate of Chemical Sciences since 2003. Assistant Professor of Kirovograd State Pedagogical University.
Field of scientific interests: chemistry of cagelike compounds.
Rights and permissions
About this article
Cite this article
Kas’yan, L.I., Kas’yan, A.O. & Golodaeva, E.A. Methods and mechanisms of epoxy compounds reduction. Russ J Org Chem 44, 153–183 (2008). https://doi.org/10.1134/S1070428008020012
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428008020012