Abstract
A reaction of simple α,ω-dithiolates with (+)-3-carene and (-)-6h-pinene p-nitroso chlorides goes through the substitution for the chlorine atoms at the quaternary carbon atoms with retention of configuration leading to the corresponding bis-6h-sulfanyl oximes. Their reaction with dichloromethane under conditions of phase-transfer catalysis takes place at the oxime hydroxyl and gives sulfur-containing macrocyclic compounds.
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P. A. Petukhov, S. N. Bizyaev, A. V. Tkachev, Izv. Akad. Nauk, Ser. Khim., 2001, 2013 [Russ. Chem. Bull., Int. Ed., 2001, 50, 2106].
S. V. Larionov, A. V. Tkachev, Russ. Khim. Zh., 2004, 48, No. 4, 154 [Mendeleev Chem. J. (Engl. Transl.), 2004, 48, No. 4].
S. V. Larionov, L. L Myachina, R. F. Klevtsova, L. A. Glinskaya, L. A. Sheludyakova, S. N. Bizyaev, A. V. Tkachev, Dokl. Akad. Nauk, 2004, 397, 1 [Dokl. Chem. (Engl. Transl.), 2004].
S. V. Larionov, L. I. Myachina, L. A. Sheludyakova, E. G. Boguslavskii, S.N. Bizyaev, A. V. Tkachev, Zh. Neorg. Khim., 2007, 52, 47 [Russ. J. Inorg. Chem. (Engl. Transl.), 2007, 52].
S. V. Larionov, A. V. Tkachev, L. I. Myachina, S. N. Bizyaev, L. A. Glinskaya, R. F. Klevtsova, Dokl. Akad. Nauk, 2006, 411, 198 [Dokl. Chem. (Engl. Transl.), 2006].
S. V. Larionov, L. I. Myachina, R. F. Klevtsova, L. A. Glinskaya, L. A. Sheludyakova, S. N. Bizyaev, A. V. Tkachev, Zh. Neorg. Khim., 2005, 50, 582 [Russ. J. Inorg. Chem. (Engl. Transl.), 2005, 50].
R. D. Adams, J. L. Perrin, J. A. Queisser, R. D. Rogers, J. Organomet. Chem., 2000, 596, 115.
G. De Santis, L. Fabbrizzi, M. Licchelli, ?. Mangano, D. Sacchi, N. Sardone, Inorg. Chim. A., 1997, 257, 69.
A. R. Fakhari, M. R. Ganjali, M. Shamsipur, Anal. Chem., 1997, 69, 3693.
J. R. Dilworth, N. Wheatley, Coord. Chem. R., 2000, 199, 89.
I. A. Fallis, Annu. Rep. Prog. Chem., Sect. A, 2002, 98, 321.
J. Buter, R. M. Kellogg, J. Org.Chem., 1981, 46, 4481.
A. V. Tkachev, Russ. Khim. Zh., 1998, 42 (1–2), 42 [Mendeleev Chem. J. (Engl. Transl.), 2004, 42, Nos 1–2].
S. V. Larionov, T. E. Kokina, A. M. Agafontsev, N. B. Gorshkov, A. V. Tkachev, R. F. Klevtsova, L. A. Glinskaya, Koordinats. Khim., 2007, 33, 525 [Russ. J. Coord. Chem. (Engl. Transl.), 2007, 33].
?. E. Kokina, L. I. Myachina, L. A. Glinskaya, A. V. Tkachev, R. F. Klevtsova, L. A. Sheludyakova, S. N. Bizyaev, A. M. Agafontsev, N. B. Gorshkov, S. V. Larionov, Koordinats. Khim., 2008, 34, 1 [Russ. J. Coord. Chem. (Engl. Transl.), 2008, 34].
E. V. Dehmlow, S. Dehmlow, Phase Transfer Catalysis, 2nd ed., Verlag Chemie, Weinheim 1983, 397 pp.
S. V. Larionov, T. E. Kokina, A. M. Agafontsev, N. B. Gorshkov, A. V. Tkachev, R. F. Klevtsova, L. A. Glinskaya, Koordinats. Khim., 2007, 33, 525 [Russ. J. Coord. Chem. (Engl. Transl.), 2007, 33].
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1434–1438, July, 2010.
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Gorshkov, N.B., Agafontsev, A.M. & Tkachev, A.V. Synthesis of terpenoid bis-α-sulfanyl oximes and macrocycles on their basis. Russ Chem Bull 59, 1467–1471 (2010). https://doi.org/10.1007/s11172-010-0264-3
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DOI: https://doi.org/10.1007/s11172-010-0264-3