Abstract
Earlier unknown 1,3-bisketene organoelement derivatives RMeE(C(E ’Me3)=C=O)2 (E = Si, Ge; E’ = Si, Ge, Sn) have been synthesized by the reaction of bis(alkoxyethynyl)silanes and -germanes with Me3E’Hal. Bis(1-trimethylsilyl-2-oxovinyl)silane is also formed by the reaction of trimethylsilyl- and (dimethylsilylene)bisketenes with dimethylsilylene bistriflate and trimethylsilyl triflate, respectively. Addition of nucleophiles to the ketene fragment of compounds synthesized has been studied.
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S. V. Gruener, B. Wrackmeyer, R. N. Ezhov, V. S. Petrosyan, Izv. Akad. Nauk, Ser. Khim., 2003, 1641 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1730].
K. Sung, T. T. Tidwell, J. Am. Chem. Soc., 1996, 118, 2768.
A. Joffler, G. Himbert, Synthesis, 1992, 495.
S. V. Ponomarev, M. B. Erman, S. A. Lebedev, S. Ya. Pechurina, I. F. Lutsenko, Zh. Obshch. Khim., 1971, 41, 127 [J. Gen. Chem. USSR (Engl. Transl.), 1971, 41].
M. A. Kazankova, V. A. Ilyushin, I. F. Lutsenko, Zh. Obshch. Khim., 1980, 50, 690 [J. Gen. Chem. USSR (Engl. Transl.), 1980, 50].
I. V. Efimova, M. A. Kazankova, I. F. Lutsenko, Zh. Obshch. Khim., 1985, 55, 1647 [J. Gen. Chem. USSR (Engl. Transl.), 1885, 55].
R. D. Miller, D. R. Mckean, Synthesis, 1979, 730.
Yu. K. Grishin, S. V. Ponomarev, S. A. Lebedev, Zh. Org. Khim., 1974, 404 [J. Org. Chem. USSR (Engl. Transl.), 1974].
K. B. Borisenko, R. N. Yezhov, S. V. Gruener, H. E. Robertson, D. W. H. Rankin, Inorg. Chim. Acta, 2008, 361, 467.
W. Uhlig, A. Tzschach, Z. Chem., 1988, 28, 409.
S. V. Ponomarev, A. S. Zolotareva, R. N. Ezhov, Yu. V. Kuznetsov, V. S. Petrosyan, Izv. Akad. Nauk, Ser. Khim., 2001, 1045 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1093].
B. L. Groh, G. R. Magrum, T. J. Barton, J. Am. Chem. Soc. 1987, 109, 7568.
R. L. Danheiser, A. Nishida, S. Savariar, M. P. Trova, Tetrahedron Lett., 1988, 29, 4917.
S. Akai, S. Kitagaki, T. Naka, K. Jamamoto, Y. Tsusuki, K. Matsumoto, Y. Kita, J. Chem. Soc., Perkin Trans. 1, 1996, 1705.
H. Kai, K. Iwamoto, N. Chatani, Sh. Murai, J. Am. Chem. Soc., 1996, 118, 7634.
G. Maas, M. Regitz, R. Rahm, J. Schneider, P. J. Stang, Ch. M. Crittell, J. Chem. Soc., Chem. Commun., 1990, 1456.
M. G. Voronkov, Yu. I. Khudobin, Izv. Akad. Nauk SSSR, Ser. Khim., 1956, 714 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1956, 5].
V. F. Mironov, A. L. Kravchenko, Izv. Akad. Nauk SSSR, Ser. Khim., 1965, 1096 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1965, 14].
D. Seyferth, N. Kahlen, J. Org. Chem., 1960, 25, 809.
L. L. Shchukovskaya, R. I. Pal’chik, A. N. Lazarev, Dokl. Akad. Nauk SSSR, 1965, 164, 357 [Dokl. Chem. USSR (Engl. Transl.), 1965].
E. J. Corey, H. Cho, Ch. Rucker, D. H. Hua, Tetrahedron Lett., 1981, 22, 3455.
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Iodotrimethylsilane (2) is an excellent silylating agent for organic carbonyl compounds.7
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 789-793, April, 2009.
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Gruener, S.V., Ezhov, R.N. & Petrosyan, V.S. Ketene organoelement derivatives. Synthesis of bis(l-R-2-oxovinyl)silanes and germanes (R = SiMe3, GeMe3, SnMe3). Russ Chem Bull 58, 805–809 (2009). https://doi.org/10.1007/s11172-009-0098-z
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DOI: https://doi.org/10.1007/s11172-009-0098-z