Abstract
A synthetic procedure for the preparation of sterically hindered catechols and o-quinones by the reaction of catechol with cyclohexene was developed. Novel cyclohexyl substituted catechols displayed remarkable stability during redox transformations and could be used as redoxactive ligands.
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W. Ma, Y. T. Long, Chem. Soc. Rev., 2014, 43, 30; DOI: https://doi.org/10.1039/C3CS60174A.
V. S. Chedea, L. Choueiri, M. Jisaka, P. Kefalas, Food Chem., 2012, 135, 1999; DOI: https://doi.org/10.1016/j.foodchem.2012.06.094.
Q. Stéphane, K. S. Feldman, J. Org. Chem., 1997, 62, 8809; DOI: https://doi.org/10.1021/jo971354k.
K. C. Nicolaou, C. Boddy, S. Bräse, N. Winssinger, Angew. Chem., Int. Ed., 1999, 38, 2096; DOI: https://doi.org/10.1002/(SICI)1521-3773(19990802)38:15<2096::AID-ANIE2096>3.0.CO;2-F.
F. F. Paintner, K. Görler, W. Voelter, Synlett, 2003, 0522; DOI: https://doi.org/10.1055/s-2003-37506.
K. Miura, T. Inagaki, N. Nakatani, Chem. Pharm. Bull., 1989, 37, 1816, DOI: https://doi.org/10.1248/cpb.37.1816.
Y. Shen, Y. Sung, C. Chen, Eur. J. Pharmacol., 1998, 343, 79; DOI: https://doi.org/10.1016/S0014-2999(97)01519-7.
I. Kruk, T. Michalska, K. Lichszteld, A. Kiadna, H. Y. Aboul-Enein, Chemosphere, 2000, 41, 1059; DOI: https://doi.org/10.1016/S0045-6535(99)00454-3.
C. G. Pierpont, Coord. Chem. Rev., 2001, 216, 99; DOI: https://doi.org/10.1016/S0010-8545(01)00309-5.
O. Sato, J. Tao, Y.-Z. Zhang, Angew. Chem., Int. Ed., 2007, 46, 2152; DOI: https://doi.org/10.1002/anie.200602205.
G. A. Abakumov, V. I. Nevodchikov, Dokl. Akad. Nauk SSSR [Dokl. Chem. USSR], 1982, 266, 1407 (in Russian).
G. A. Abakumov, V. K. Cherkasov, M. P. Bubnov, O. G. Ellert, J. V. Dobrokhotova, L. N. Zakharov, Yu. T. Struchkov, Dokl. Akad. Nauk SSSR [Dokl. Chem. USSR], 1993, 328, 332 (in Russian).
V. Nair, R.S. Menon, A. T. Biju, K. G. Abhilash, Chem. Soc. Rev., 2012, 41, 1050; DOI: https://doi.org/10.1039/C1CS15186J.
I. S. Belostotskaya, N. L. Komissarova, E. V. Dzhuaryan, V. V. Ershov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1972, 21, 1535; DOI: https://doi.org/10.1007/BF00850511.
V. A. Kuropatov, S. V. Klementieva, G. K. Fukin, S. Yu. Ketkov, A. S. Mitin, Yu. G. Budnikova, V. K. Cherkasov, G. A. Abakumov, Tetrahedron, 2010, 66, 7605; DOI: https://doi.org/10.1016/j.tet.2010.07.038.
V. A. Kuropatov, V. K. Cherkasov, Yu. A. Kurskii, G. K. Fukin, L. G. Abakumova, G. A. Abakumov, Russ. Chem. Bull., 2006, 55, 708; DOI: https://doi.org/10.1007/s11172-006-0317-9.
G. A. Abakumov, V. K. Cherkasov, T. N. Kocherova, N. O. Druzhkov, Yu. A. Kurskii, M. P. Bubnov, G. K. Fukin, L. G. Abakumova, Russ. Chem. Bull., 2007, 56, 1849; DOI: https://doi.org/10.1007/s11172-007-0287-6.
G. K. Fukin, A. V. Cherkasov, M. P. Shurygina, N. O. Druzhkov, V. A. Kuropatov, S. A. Chesnokov, G. A. Abakumov, Struct. Chem., 2010, 21, 607; DOI: https://doi.org/10.1007/s11224-010-9590-1.
G. A. Abakumov, V. K. Cherkasov, L. G. Abakumova, N. O. Druzhkov, V. I. Nevodchikov, Yu. A. Kursky, N. P. Makarenko, Metalloorgan. Khim. [Organometallic Chem.], 1991, 4, 925 (in Russian).
G. A. Abakumov, V. K. Cherkasov, L. G. Abakumova, V. I. Nevodchikov, N. O. Druzhkov, N. P. Makarenko, Ju. A. Kursky, J. Organomet. Chem., 1996, 491, 127; DOI: https://doi.org/10.1016/0022-328X(94)05168-B.
V. K. Cherkasov, G. A. Abakumov, A. S. Shavyrin, V. V. Kuz’michev, E. V. Baranov, I. V. Smolyaninov, V. A. Kuropatov, Asian J. Org. Chem., 2015, 4, 446; DOI: https://doi.org/10.1002/ajoc.201500005.
Ya. B. Kozlikovsky, V. A. Koschii, S. A. Butov, T. F. Ovsiyuk, Zh. Org. Khim. [J. Org. Chem.], 1988, 24, 827 (in Russian).
G. A. Abakumov, N. N. Vavilina, Y. A. Kurskii, V. I. Nevodchikov, V. K. Cherkasov, A. S. Shavyrin, Russ. Chem. Bull., 2003, 52, 1847; DOI: https://doi.org/10.1023/A:1026029410312.
A. F. Markov, A. E. Procenko, N. V. Kandalintseva, Chem. Sustain. Dev., 2007, 15, 557.
G. A. Abakumov, V. A. Muraev, Dokl. Akad. Nauk SSSR [Dokl. Chem. USSR], 1974, 217, 1313 (in Russian).
A. Weissberger, E. S. Proskauer, J. A. Riddick, E. E. Toops, Organic Solvents. Physical Properties and Methods of Purification, Intersci. Publ., New York-London, 1955.
K. A. Martyanov, V. K. Cherkasov, G. A. Abakumov, M. A. Samsonov, V. V. Khrizanforova, Y. H. Budnikova V. A. Kuropatov, Dalton Trans., 2016, 45, 7400, DOI: https://doi.org/10.1039/C6DT00769D.
SAINT Data Reduction and Correction v. 8.38A, Bruker AXS, 2017, Madison (WI), USA.
G. M. Sheldrick, SHELXTL, V. 6.14. Structure Determination Software Suite; Madison (WI), USA.
G. M. Sheldrick, SADABS v.2016/2, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison (WI), USA.
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This work was financially supported by the Russian Science Foundation (Project No. 19-13-00142). The studies were carried out using the equipment of the Center for Collective Use “Analytical Center of the IMCh RAS” at the G. A. Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences and supported by the Federal Target Program “Research and Development on Priority Directions of Scientific and Technological Complex of Russia for 2014-2020” (unique project identifier RFMEFI62120X0040).
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Kocherova, T.N., Druzhkov, N.O., Martyanov, K.A. et al. Alkylation of catechol with cyclohexene. Novel sterically hindered o-quinones and catechols. Russ Chem Bull 69, 2383–2389 (2020). https://doi.org/10.1007/s11172-020-3051-9
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DOI: https://doi.org/10.1007/s11172-020-3051-9