Abstract
The review systematizes and generalizes modern approaches to the synthesis of ethers using metal complex catalysts.
Similar content being viewed by others
References
Golubeva, I.A. and Tolstykh, L.I., Osnovy tekhnologii neftekhimicheskogo sinteza i proizvodstva prisadok (Principles of Technologies of Petrochemical Synthesis and Manufacture of Additives), Moscow: GANG, 1996.
Hydrocarbon Chemistry, Olah, G.A. and Molnár, Á., Eds., New York: Wiley, 2003, p. 1.
Greene, T.W. and Wuts, P.G.M., Protective Groups in Organic Synthesis, New York: Wiley, 1999, 3rd ed., p. 23.
McCloskey, C.M., Adv. Carbohydr. Chem., 1957, vol. 12, p. 137. doi https://doi.org/10.1016/S0096-5332(08)60207-6
Kasprzycka, A., Ptaszek-Budniok, A., and Szeja, W., Synth. Commun., 2014, vol. 44, p. 2276. doi https://doi.org/10.1080/00397911.2014.894526
Liu, Y., Hua, R., Sun, H.-B., and Qiu, X., Organometallics, 2005, vol. 24, p. 2819. doi https://doi.org/10.1021/om049040s
Zhu, Z. and Espenson, J.H., J. Org. Chem., 1996, vol. 61, p. 324. doi https://doi.org/10.1021/jo951613a
Bikard, Y., Mezaache, R., Weibel, J.-M., Benkouider, A., Sirlin, C., and Pale, P., Tetrahedron, 2008, vol. 64, p. 10224. doi https://doi.org/10.1016/j.tet.2008.08.026
Bikard, Y., Weibel, J.M., Blanc, A., and Pale, P., Tetrahedron Lett., 2007, vol. 48, p. 8895. doi https://doi.org/10.1016/j.tetlet.2007.10.045
Yadav, J.S., Bhunia, D.C., Krishna, K.V., and Srihari, P., Tetrahedron Lett., 2007, vol. 48, p. 8306. doi https://doi.org/10.1016/j.tetlet.2007.09.140
Sherry, B.D., Radisevich, A.T., and Toste, F.D., J. Am. Chem. Soc., 2003, vol. 125, p. 6076. doi https://doi.org/10.1021/ja0343050
Kuninobu, Y., Ueda, H., and Takai, K., Chem. Lett., 2008, vol. 37, p. 878. doi https://doi.org/10.1246/cl.2008.878
Cuenca, A.B., Mancha, G., Asensio, G., and Medio-Simon, M., Chem. Eur. J., 2008, vol. 14, p. 1518. doi https://doi.org/10.1002/chem.200701134
Jiang, X., London, E.K., Morris, D.J., Clarkson, G.J., and Wills, M., Tetrahedron, 2010, vol. 66, p. 9828. doi https://doi.org/10.1016/j.tet.2010.10.068
Georgy, M., Boucard, V., Debleds, O., Dal Zotto, C., and Campagne, J.M., Tetrahedron, 2009, vol. 65, p. 1758. doi https://doi.org/10.1016/j.tet.2008.12.051
Veenboer, R.M.P. and Nolan, S.P., Green Chem., 2015, vol. 17, p. 3819. doi https://doi.org/10.1039/c5gc00684h
Kim, J., Lee, D.-H., Kalutharage, N., and Yi, C.S., ACS Catal., 2014, vol. 4, p. 3881. doi https://doi.org/10.1021/cs5012537
Miller, K.J. and Abu-Omar, M.M., Eur. J. Org. Chem., 2003, p. 1294. doi https://doi.org/10.1002/ejoc.200390185
Biswas, S. and Samec, J.S.M., Chem. Asian J., 2013, vol. 8, p. 974. doi https://doi.org/10.1002/asia.201201178
Zhan, Z.-P., Yu, J.-L., Cui, Y.-Y., Yang, R.-F., Yang, W.-Z., and Li, J.-P., J. Org. Chem., 2006, vol. 71, p. 8298. doi https://doi.org/10.1021/jo061234p
Salehi, F., Iranpoor, N., and Behbahani, F.K., Tetrahedron, 1998, vol. 54, p. 943. doi https://doi.org/10.1016/S0040-4020(97)10350-7
Namboodiri, V.V. and Varma, R.S., Tetrahedron Lett., 2002, vol. 43, p. 4593. doi https://doi.org/10.1016/S0040-4039(02)00890-0
Sharma, G.V.M., Prasad, T.R., and Mahalingam, A.K., Tetrahedron Lett., 2001, vol. 42, p. 759. doi https://doi.org/10.1016/S0040-4039(00)02108-0
Moghadam, B.N., Akhlaghinia, B., and Rezazadeh, S., Res. Chem. Intermed., 2016, vol. 42, p. 1487. doi https://doi.org/10.1007/s11164-015-2098-y
Mezaache, R., Dembelé, Y.A., Bikard, Y., Weibel, J.M., Blanc, A., and Pale, P., Tetrahedron Lett., 2009, vol. 50, p. 7322. doi https://doi.org/10.1016/j.tetlet.2009.10.053
Khusnutdinov, R.I., Bayguzina, A.R., Gimaletdinova, L.I., and Dzhemilev, U.M., Russ. J. Org. Chem., 2012, vol. 48, p. 1191. doi https://doi.org/10.1134/S1070428012090072
Dzhemilev, U.M., Khusnutdinov, R.I. Baiguzina, A.R., and Rasulev, T.V., RU Patent no. 2433 991, 2011; Chem. Abstr., 2011, vol. 155, no. 656 550.
Bayguzina, A.R., Gimaletdinova, L.I., and Khusnutdinov, R.I., Russ. J. Org. Chem., 2018, vol. 54, p. 1148. doi https://doi.org/10.1134/S1070428018080055
Dzhemilev, U.M., Khusnutdinov, R.I., Baiguzina, A.R., and Gimaletdinova, L.I., RU Patent no. 2536486, 2014; Chem. Abstr., 2014, vol. 162, no. 106729.
Khusnutdinov, R.I., Bayguzina, A.R., Mukminov, R.R., Gimaletdinova, L.I., and Dzhemilev, U.M., Arkivoc, 2014, part (iv), p. 342. doi https://doi.org/10.3998/ark.5550190.p008.393
Dzhemilev, U.M., Khusnutdinov, R.I., Baiguzina, A.R., Aminov, R.I., Mukminov, R.R., Gimaletdinova, L.I., and Litvinchuk, V.E., RU Patent no. 2582620, 2016; Chem. Abstr., 2016, vol. 164, no. 483 519.
Bayguzina, A.R., Gimaletdinova, L.I., and Khusnutdinov, R.I., Russ. J. Org. Chem., 2017, vol. 53, p. 1840. doi https://doi.org/10.1134/S1070428017120090
Dzhemilev, U.M., Khusnutdinov, R.I., Baiguzina, A.R., and Gimaletdinova, L.I., RU Patent no. 2644163, 2018. Chem. Abstr., 2018, vol. 168, no. 254843.
Kraatz, U., Chem. Ber., 1973, vol. 106, p. 3095. doi https://doi.org/10.1002/cber.19731060941
Schlummer, B. and Scholz, U., Adv. Synth. Catal., 2004, vol. 346, p. 1599. doi https://doi.org/10.1002/adsc.200404216
Burgos, C.H., Barder, T.E., Huang, X., and Buchwald, S.L., Angew. Chem., Int. Ed., 2006, vol. 45, p. 4321.
Gowrisankar, S., Sergeev, A.G., Anbarasan, P., Spannenberg, A., Neumann, H., and Beller, M., J. Am. Chem. Soc., 2010, vol. 132, p. 11592. doi https://doi.org/10.1021/ja103248d
Akkoç, M., Gürbüz, N., Çetinkaya, E., and Özdemir, I., Synlett., 2008, p. 1781. doi https://doi.org/10.1055/s-2008-1078548
Cheung, C.W. and Buchwald, S.L., Org. Lett., 2013, vol. 15, p. 3966. doi https://doi.org/10.1021/ol401796v
Parrish, C.A. and Buchwald, S.L., J. Org. Chem., 2001, vol. 66, p. 2498. doi https://doi.org/10.1021/jo001426z
Anderson, K.W., Ikawa, T., Tundel, R.E., and Buchwald, S.L., J. Am. Chem. Soc., 2006, vol. 128, p. 10694. doi https://doi.org/10.1021/ja0639719
Dzhemilev, U.M., Khusnutdinov, R.I., Shchadneva, N.A., and Malikov, A.I., RU Patent no. 2145593, 1998. Chem. Abstr., 2001, vol. 135, no. 210774.
Khusnutdinov, R.I., Shchadneva, N.A., Malikov, A.I., and Dzhemilev, U.M., Pet. Chem., 2000, vol. 40, p. 419.
Iwanami, K., Seo, H., Tobita, Y., and Oriyama, T., Synthesis, 2005, p. 183. doi https://doi.org/10.1055/s-2004-834942
Evano, G., Blanchard, N., and Toumi, M., Chem. Rev., 2008, vol. 108, p. 3054. doi https://doi.org/10.1021/cr8002505
Miao, T. and Wang, L., Tetrahedron Lett., 2007, vol. 48, p. 95. doi https://doi.org/10.1016/j.tetlet.2006.11.001
Huang, J., Chen, Y., Chan, J., Ronk, M.L., Larsen, R.D., and Faul, M.M., Synlett, 2011, p. 1419. doi https://doi.org/10.1055/s-0030-1260761
Chang, J.W.W., Chee, S., Mak, S., Buranaprasertsuk, P., Chavasiri, W., and Chan, P.W.H., Tetrahedron Lett., 2008, vol. 49, p. 2018. doi https://doi.org/10.1016/j.tetlet.2008.01.062
Altman, R.A., Shafir, A., Lichtor, P.A., and Buchwald, S.L., J. Org. Chem., 2008, vol. 73, p. 284. doi https://doi.org/10.1021/jo702024p
Hosseinzadeh, R., Tajbakhsh, M., Mohadjerani, M., and Alikarami, M., Synlett, 2005, no. 7, p. 1101. doi https://doi.org/10.1055/s-2005-865198
Zhang, H., Ma, D., and Cao, W., Synlett, 2007, p. 243. doi https://doi.org/10.1055/s-2007-968010
Ma, D. and Cai, Q., Org. Lett., 2003, vol. 5, p. 3799. doi https://doi.org/10.1021/ol0350947
Chen, W., Li, J., Fang, D., Feng, C., and Zhang, C., Org. Lett., 2008, vol. 10, p. 4565. doi https://doi.org/10.1021/ol801730g
Wolter, M., Nordmann, G., Job, G.E., and Buchwald, S.L., Org. Lett., 2002, vol. 4, p. 973. doi https://doi.org/10.1021/ol025548k
Gujadhur, R. and Venkataraman, D., Synth. Commun., 2001, vol. 31, p. 2865. doi https://doi.org/10.1081/SCC-100105338
Gujadhur, R.K., Bates, C.G., and Venkataraman, D., Org. Lett., 2001, vol. 3, p. 4315. doi https://doi.org/10.1021/ol0170105
Chen, Y.-J. and Chen, H.-H., Org. Lett., 2006, vol. 8, p. 5609. doi https://doi.org/10.1021/ol062339h
Naidu, A.B., Raghunath, O.R., Prasad, D.J.C., and Sekar, G., Tetrahedron Lett., 2008, vol. 49, p. 1057. doi https://doi.org/10.1016/j.tetlet.2007.11.203
Buck, E., Song, Z.J., Tschaen, D., Dormer, P.G., Volante, R.P., and Reider, P.J., Org. Lett., 2002, vol. 4, p. 1623. doi https://doi.org/10.1021/ol025839t
Monnier, F. and Taillefer, M., Angew. Chem., Int. Ed., 2009, vol. 48, p. 6954. doi https://doi.org/10.1002/anie.200804497
Xia, N. and Taillefer, M., Chem. Eur. J., 2008, vol. 14, p. 6037. doi https://doi.org/10.1002/chem.200800436
Taillefer, M., Xia, N., and Ouali, A., PCT Patent Appl. Pub. no. WO2008004088 A2, 2008; Chem. Abstr., 2008, vol. 148, no. 144 205.
Cristau, H.-J., Cellier, P.P., Hamada, S., Spindler, J.-F., and Taillefer, M., Org. Lett., 2004, vol. 6, p. 913. doi https://doi.org/10.1021/ol036290g
Schareina, T., Zapf, A., Cotte, A., Muller, N., and Beller, M., Tetrahedron Lett., 2008, vol. 49, p. 1851. doi https://doi.org/10.1016/j.tetlet.2008.01.036
Niu, J., Zhou, H., Li, Z., Xu, J., and Hu, S., J. Org. Chem., 2008, vol. 73, p. 7814. doi https://doi.org/10.1021/jo801002c
Manbeck, G.F., Lipman, A.J., Stockland, R.A., Freidl, A.L., Hasler, A.F., Stone, J.J., and Guzei, I.A., J. Org. Chem., 2005, vol. 70, p. 244. doi https://doi.org/10.1021/jo048761y
Kidwai, M., Mishra, N.K., Bansal, V., Kumar, A., and Mozumdar, S., Tetrahedron Lett., 2007, vol. 48, p. 8883. doi https://doi.org/10.1016/j.tetlet.2007.10.050
Lipshutz, B.H., Unger, J.B., and Taft, B.R., Org. Lett., 2007, vol. 9, p. 1089. doi https://doi.org/10.1021/ol0700409
Liu, Y. and Zhang, S., Synlett, 2011, p. 268. doi https://doi.org/10.1055/s-0030-1259291
Kundu, D., Maity, P., and Ranu, B.C., Org. Lett., 2014, vol. 16, p. 1040. doi https://doi.org/10.1021/ol500134p
Paul, R., Ali, M.A., and Punniyamurthy, T., Synthesis, 2010, p. 4268. doi https://doi.org/10.1055/s-0030-1258965
Smith, K. and Jones, D., J. Chem. Soc., Perkin Trans. 1, 1992, p. 407. doi https://doi.org/10.1039/P19920000407
Zadmard, R., Aghapoor, K., Bolourtchian, M., and Saidi, M.R., Synth. Commun., 1998, vol. 28, p. 4495. doi https://doi.org/10.1080/00397919808004511
Kim, H.J., Kim, M., and Chang, S., Org. Lett., 2011, vol. 13, p. 2368. doi https://doi.org/10.1021/ol200603c
Quach, T.D. and Batey, R.A., Org. Lett., 2003, vol. 5, p. 1381. doi https://doi.org/10.1021/ol034454n
Evans, D.A., Katz, J.L., and West, T.R., Tetrahedron Lett., 1998, vol. 39, p. 2937. doi https://doi.org/10.1016/S0040-4039(98)00502-4
Sagar, A.D., Tale, R.H., and Adude, R.N., Tetrahedron Lett., 2003, vol. 44, p. 7061. doi https://doi.org/10.1016/S0040-4039(03)01776-3
Tale, R.H. and Patil, K.M., Tetrahedron Lett., 2002, vol. 43, p. 9715. doi https://doi.org/10.1016/S0040-4039(02)02256-6
Tale, R.H., Patil, K.M., and Dapurkar, S.E., Tetrahedron Lett., 2002, vol. 44, p. 3427. doi https://doi.org/10.1016/S0040-4039(03)00035-2
Chan, D.M.T., Monaco, K.L., Wang, R.-P., and Winteres, M.P., Tetrahedron Lett., 1998, vol. 39, p. 2933. doi https://doi.org/10.1016/S0040-4039(98)00503-6
Tzschucke, C.C., Murphy, J.M., and Hartwig, J.F., Org. Lett., 2007, vol. 9, p. 761. doi https://doi.org/10.1021/ol062902w
Kuwano, R. and Kusano, H., Org. Lett., 2008, vol. 10, p. 1979. doi https://doi.org/10.1021/ol800548t
Yatusmonji, Y., Ishida, Y., Tsubouchi, A., and Takeda, T., Org. Lett., 2007, vol. 9, p. 4603. doi https://doi.org/10.1021/ol702122d
Zolfigol, M.A., Mohammadpoor-Baltork, I., Habibi, D., Mirjalili, B.F., and Bamoniri, A., Tetrahedron Lett., 2003, vol. 44, p. 8165. doi https://doi.org/10.1016/j.tetlet.2003.09.036
Iwanami, K. and Oriyama, T., Chem. Lett., 2004, vol. 33, p. 1324. doi https://doi.org/10.1246/cl.2004.1324
Savela, R. and Leino, R., Synthesis, 2015, vol. 47, p. 1749. doi https://doi.org/10.1055/s-0034-1380155
Kalutharage, N. and Yi, C.S., Org. Lett., 2015, vol. 17, p. 1778. doi https://doi.org/10.1021/acs.orglett.5b00553
Gooßen, L.J. and Linder, C., Synlett, 2006, p. 3489. doi https://doi.org/10.1055/s-2006-956484
Lopez, F., Ohmura, T., and Hartwig, J.F., J. Am. Chem. Soc., 2003, vol. 125, p. 3426. doi https://doi.org/10.1021/ja029790y
Leitner, A., Shu, C., and Hartwig, J.F., Org. Lett., 2005, vol. 7, p. 1093. doi https://doi.org/10.1021/ol050029d
Ammann, S.E., Rice, G.T., and White, M.C., J. Am. Chem. Soc., 2014, vol. 136, p. 10834. doi https://doi.org/10.1021/ja503322e
Trend, R.M., Ramtohul, Y.K., Ferreira, E.M., and Stoltz, B., Angew. Chem., Int. Ed., 2003, vol. 42, p. 2892. doi https://doi.org/10.1002/anie.200351196
Qian, H., Han, X., and Widenhoefer, R.A., J. Am. Chem. Soc., 2004, vol. 126, p. 9536. doi https://doi.org/10.1021/ja0477773
Yang, C.-G., Reich, N.W., Shi, Z., and He, C., Org. Lett., 2005, vol. 7, p. 4553. doi https://doi.org/10.1021/ol051065f
Dzudza, A. and Marks, T.J., Org. Lett., 2009, vol. 11, p. 1523. doi https://doi.org/10.1021/ol8029559
Murayama, H., Nagao, K., Ohmiya, H., and Sawamura, M., Org. Lett., 2015, vol. 17, p. 2039. doi https://doi.org/10.1021/acs.orglett.5b00758
Wolfe, J.P. and Rossi, M.A., J. Am. Chem. Soc., 2004, vol. 126, p. 1620. doi https://doi.org/10.1021/ja0394838
Fujino, D., Yorimitsu, H., and Osuka, A., J. Am. Chem. Soc., 2014, vol. 136, p. 6255. doi https://doi.org/10.1021/ja5029028
Zhang, Z., Liu, C., Kinder, R.E., Han, X., Qian, H., and Widenhoefer, R.A., J. Am. Chem. Soc., 2006, vol. 128, p. 9066. doi https://doi.org/10.1021/ja062045r
Zhang, G., Cui, L., Wang, Y., and Zhang, L., J. Am. Chem. Soc., 2010, vol. 132, p. 1474. doi https://doi.org/10.1021/ja909555d
Nordmann, G. and Buchwald, S.L., J. Am. Chem. Soc., 2003, vol. 125, p. 4978. doi https://doi.org/10.1021/ja034809y.
Ball, L.T., Green, M., Lloyd-Jones, G.C., and Russel, C.A., Org. Lett., 2010, vol. 12, p. 4724. doi https://doi.org/10.1021/ol1019162
Cui, D.-M., Yu, K.-R., and Zhang, C., Synlett, 2009, p. 1103. doi https://doi.org/10.1055/s-0028-1088158
Veenboer, R.M.P., Dupuy, S., and Nolan, S.P., ACS Catal., 2015, vol. 5, p. 1330. doi https://doi.org/10.1021/cs501976s
Dick, A.R., Hull, K.L., and Sanford, M.S., J. Am. Chem. Soc., 2004, vol. 126, p. 2300. doi https://doi.org/10.1021/ja031543m
Desai, L.V., Malik, H.A., and Sanford, M.S., Org. Lett., 2006, vol. 8, p. 1141. doi https://doi.org/10.1021/ol0530272
Wang, G.-W. and Yuan, T.-T., J. Org. Chem., 2010, vol. 75, p. 476. doi https://doi.org/10.1021/jo902139b
Jiang, T.-S. and Wang, G.-W., J. Org. Chem., 2012, vol. 77, p. 9504. doi https://doi.org/10.1021/jo301964m
Shi, S. and Kuang, C., J. Org. Chem., 2014, vol. 79, p. 6105. doi https://doi.org/10.1021/jo5008306
Khusnutdinov, R.I., Bayguzina, A.R., Gallyamova, L.I., and Dzhemilev, U.M., Pet. Chem., 2012, vol. 52, p. 261. doi https://doi.org/10.1134/S0965544112040044
Dzhemilev, U.M., Khusnutdinov, R.I., Baiguzina, A.R., and Gallyamova, L.I., RU Patent no. 2447054, 2012; Chem. Abstr., 2012, vol. 156, no. 505198.
Khusnutdinov, R.I., Baiguzina, A.R., and Dzhemilev, U.M., Organicheskie i neorganicheskie gipogalogenity v organicheskom sinteze (Organic and Inorganic Hypohalites in Organic Synthesis), Moscow: Nauka, 2016, p. 277.
Khusnutdinov, R.I., Baiguzina, A.R., and Dzhemilev, U.M., Russ. J. Org. Chem., 2017, vol. 53, p. 1113. doi https://doi.org/10.1134/S1070428017080012
Khusnutdinov, R.I., Schadneva, N.A., Bayguzina, A.R., Lavrentieva, Yu.Yu., Dzhemilev, U.M., Burangulova, R.Yu., and Smirnov, A.A., Arkivoc, 2004, part (xi), p. 53. doi https://doi.org/10.3998/ark.5550190.0005.b08
Khusnutdinov, R.I., Shchadneva, N.A., Baiguzina, A.R., Mukminov, R.R., Mayakova, Yu.Yu., Smirnov, A.A., and Dzhemilev, U.M., Pet. Chem., 2008, vol. 48, p. 471. doi https://doi.org/10.1134/S0965544108060121
Khusnutdinov, R.I., Baiguzina, A.R., Mukminov, R.R., and Dzhemilev, U.M., Russ. J. Appl. Chem., 2009, vol. 82, p. 340. doi https://doi.org/10.1134/S1070427209020335
Khusnutdinov, R.I., Baiguzina, A.R., Mukminov, R.R., Akhmetov, I.V., Gubaidullin, I.M., Spivak, S.I., and Dzhemilev, U.M., Russ. J. Org. Chem., 2010, vol. 46, p. 1053. doi https://doi.org/10.1134/S1070428010070158
Khusnutdinov, R.I., Baiguzina, A.R., and Mukminov, R.R., Russ. J. Org. Chem., 2010, vol. 46, p. 1399. doi https://doi.org/10.1134/S1070428010090228
Khusnutdinov, R.I., Baiguzina, A.R., and Mukminov, R.R., Russ. J. Org. Chem., 2011, vol. 47, p. 437. doi https://doi.org/10.1134/S1070428011030195
Khusnutdinov, R.I., Bayguzina, A.R., and Mukminov, R.R., Russ. Chem. Bull., Int. Ed., 2013, vol. 62, p. 93. doi https://doi.org/10.1007/s11172-013-0012-6
Khusnutdinov, R.I., Bayguzina, A.R., Denisov, K.Y., and Dzhemilev, U.M., Mendeleev Commun., 2015, vol. 25, p. 219. doi https://doi.org/10.1016/j.mencom.2015.05.021
Bayguzina, A.R., Erokhina, I.S., and Khusnutdinov, R.I., Russ. J. Org. Chem., 2017, vol. 53, p. 359. doi https://doi.org/10.1134/S1070428017030071
Baiguzina, A.R., Erokhina, I.S., and Khusnutdinov, R.I., Russ. J. Gen. Chem., 2017, vol. 87, p. 389. doi https://doi.org/10.1134/S1070363217030057
Bayguzina, A.R., Tarisova, L.I., and Khusnutdinov, R.I., Russ. J. Gen. Chem., 2018, vol. 88, p. 208. doi https://doi.org/10.1134/S1070363218020056
Funding
This work was performed under financial support by the Russian Foundation for Basic Research (project no. 17-43-020 155 p_a), as well as in the framework of state assignment no. AAAA-A19-119022290009-3.
Author information
Authors and Affiliations
Corresponding author
Additional information
Conflict of Interests
The authors declare no conflict of interests.
Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 7, pp. 991–1023.
Rights and permissions
About this article
Cite this article
Khusnutdinov, R.I., Bayguzina, A.R. Metal Complex Catalysis in the Synthesis of Ethers. Russ J Org Chem 55, 903–932 (2019). https://doi.org/10.1134/S1070428019070017
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428019070017