Abstract
In a reaction of 3,6-di(tert-butyl)-4-chloro-1,2-benzoquinone with potassium ethyl xanthate, the halogen atom was replaced by the ethyl xanthate group. Acid hydrolysis of the product gave 4,7-di(tert-butyl)-5,6-dihydroxy-1,3-benzodithiol-2-one containing a pyrocatechol fragment, which was oxidized into the corresponding quinone. When irradiated in solution with visible light, this quinone quantitatively eliminated a CO molecule with contraction of the ring to a five-membered one. The quinones obtained were studied as ligands in coordination spheres of metals by ESR spectroscopy.
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G. A. Abakumov, V. K. Cherkasov, L. G. Abakumova, V. I. Nevodchikov, N. O. Druzhkov, N. P. Makarenko, and Yu. A. Kursky, J. Organomet. Chem., 1995, 491, 127.
G. A. Abakumov, V. I. Nevodchikov, N. V. Zaitova, N. O. Druzhkov, L. G. Abakumova, Yu. A. Kurskii, and V. K. Cherkasov, Izv. Akad. Nauk, Ser. Khim., 1997, 2206 [Russ. Chem. Bull., 1997, 46, 2093 (Engl. Transl.)].
M. Bogemann, S. Petersen, O. E. Schultz, and H. Soll, in Methoden der Organischen Chemie, Ed. E. Müller, Houben-Weyl, Berlin, 1955, Vol. IV, p. 804.
A. M. Sipyagin, S. V. Pal’tsun, A. V. Piyuk, N. N. Sveshnikov, V. I. Kozlovskii, and Z. G. Aliev, Zh. Org. Khim., 1993, 29, 1872 [Russ. J. Org. Chem., 1993, 29 (Engl. Transl.)].
T. Khan, J. J. W. McDouall, E. J. L. McInnes, P. J. Skabara, P. Frere, S. J. Coles, and M. B. Hursthouse, J. Mater. Chem., 2003, 13, 2490.
V. B. Vol’eva, V. V. Ershov, I. S. Belostotskaya, and N. L. Komissarov, Izv. Akad. Nauk SSSR, Ser. Khim., 1974, 739 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1974, 23 (Engl. Transl.)].
G. A. Abakumov, N. N. Vavilina, L. N. Zakharov, Yu. A. Kurskii, V. I. Nevodchikov, and A. S. Shavyrin, Izv. Akad. Nauk, Ser. Khim., 2004, 2179 [Russ. Chem. Bull., Int. Ed., 2004, 53, 2276].
N. S. Belostotskaya, N. L. Komissarova, E. V. Dzhuaryan, and V. V. Ershov, Izv. Akad. Nauk SSSR, Ser. Khim., 1973, 1380 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1973, 22 (Engl. Transl.)].
V. A. Garnov, V. I. Nevodchikov, G. A. Abakumov, V. K. Cherkasov, L. G. Abakumova, and Yu. A. Kurskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1985, 2793 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985, 34, 2589 (Engl. Transl.)].
A. Weissberger, E. S. Proskauer, J. A. Riddick, and E. E. Toops, Organic Solvents. Physical Properties and Methods of Purification, Interscience Publ., New York-London, 1955.
V. A. Muraev, G. A. Abakumov, and G. A. Razuvaev, Dokl. Akad. Nauk SSSR, 1974, 217, 1083 [Dokl. Chem., 1974 (Engl. Transl.)].
G. A. Abakumov, V. K. Cherkasov, A. V. Lobanov, and G. A. Razuvaev, Izv. Akad. Nauk SSSR, Ser. Khim., 1984, 1610 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1984, 33, 1478 (Engl. Transl.)].
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 683–686, April, 2006.
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Kuropatov, V.A., Cherkasov, V.K., Kurskii, Y.A. et al. A reaction of 3,6-di(tert-butyl)-4-chloro-1,2-benzoquinone with potassium ethyl xanthate. New sulfur-containing o-quinones. Russ Chem Bull 55, 708–711 (2006). https://doi.org/10.1007/s11172-006-0317-9
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DOI: https://doi.org/10.1007/s11172-006-0317-9