Abstract
The earlier unknown Si-fluorinated 2,8-dioxa-5-chalcogenosilocanes RFSi(OCH2CH2)2Y (R = Ph, F; Y = O, S) were synthesized. According to calculations, there is a weak transannular coordinate interaction Y→Si (Y = O, S), which is much weaker than that in the isostructural quasisilatranes (Y = N). At low temperatures, 1,1-difluoro-2,5,8-trioxasilocane forms a dimer, in which two molecules of the monomer are linked by four fluorine bridges Si-F→Si located in pairs in the two orthogonal planes SiF2Si.
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Krieble, R.H. and Burkhard, C.A., J. Am. Chem. Soc., 1947, vol. 69, no. 11, p. 2689.
Davydova, V.P., Voronkov, M.G., and Dolgov, B.N., Khimiya i prakticheskoe primenenie kremniiorganicheskikh soedinenii. Trudy konf. Kremniiorganicheskie monomery (Chemistry and Practical Application of Organosilicon Compounds. Proc. Conf. Organosilicon Monomers), Leningrad: TsBTI, 1958, no. 1, p. 204.
Voronkov, M.G. and Romadan, Yu.P., Khim. Geterotsikl. Soedin., 1966, vol. 2, no. 6, p. 671.
D’yakov, V.M., Kir’yanova, A.N., Kireeva, L.N., Chernyshev, A.E., Bochkarev, V.N., and Androsenko, S.I., Zh. Obshch. Khim., 1988, vol. 58, no. 3, p. 539.
Voronkov, M.G., Davydova, V.P., and Dolgov, B.N., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1958, no. 6, p. 698.
Piekos, B.R., Sujecki, R., and Sankowski, M., Z. Anorg. Allg. Chem., 1979, vol. 454, p. 187.
Urtane, I.P., Zelchan, G.I., and Lukevics, E., Z. Anorg. Allg. Chem., 1985, vol. 520, p. 179.
D’yakov, V.M. and Orlov, G.I., Srednie azotsoderzhashchie silatsiklany (Medium Nitrogen- Containing Silacicanes), Moscow: NIITEKHIM, 1985, pp. 1–60.
Birgele, I.S., Kemme, A.A., Kupche, E.L., Liepinsh, E.E., Mazheika, I.B., and Shatts, V.D., Kremniiorganicheskie proizvodnye aminospirtov (Organosilicon Derivatives of Amino Alcohols), Lukevits, E.Ya., Ed., Riga: Zinatne, 1987.
Corey, J.Y., Rath, N.P., John Ch.S., and Corey, E.R., J. Organomet. Chem., 1990, vol. 399, no. 3, p. 221.
Ziche, W., Ziemer, B., John, P., Weis, J., and Auner, N., J. Organomet. Chem., 1996, vol. 521, nos. 1–2, p. 29.
Selina A.A., Karlov, S.S., and Zaitseva, G.S., Khim. Geterotsikl. Soedin., 2006, vol. 42, no. 12, p. 1518.
Voronkov, M.G., Grebneva, E.A., Trofimova, O.M., Albanov, A.I., Chernov, N.F., and Chipanina, N.N., Zh. Obshch. Khim., 2006, vol. 76, no. 12, p. 1851.
Voronkov, M.G., Albanov, A.I., Grebneva, E.A., Trofimova, O.M., Chernov, N.F., Chipanina, N.N., Zh. Obshch. Khim., 2006, vol. 76, no. 12, p. 1942.
Voronkov, M.G., Khim. Geterotsikl. Soedin., 2007, vol. 43, no. 7, p. 938.
Korlyukov, A.A., Lyssenko, K.A., Antipin, M.Yu., Grebneva, E.A., Albanov, A.I., Trofimova, O.M., Zel’bst, E.A., and Voronkov, M.G., J. Organomet. Chem., 2009, vol. 694, no. 5, p. 607.
Voronkov, M.G., Korlyukov, A.A., Zel’bst, E.A., Grebneva, E.A., Trofimova, O.M., and Antipin, M.Yu., Dokl. Akad. Nauk, 2008, vol. 418, no. 4, p. 486.
Voronkov, M.G., Boyarkina, E.V., Gebel, I.A., Albanov, A.I., and Basenko, S.V., Zh. Obshch. Khim., 2005, vol. 75, no. 12, p. 2018.
Voronkov, M.G., Shevchenko, S.G., Brodskaya, E.I., Baryshok, V.P., D’yakov, V.M., Frolov, Yu.L., Raikh, P., and Anisimova, I..L., IR and Raman Spectra of Silatranes and Model Compounds. Catalog of Spectra, Novosibirsk, 1985, no. 31.
Voronkov, M.G., Korlyukov, A.A., Zel’bst, E.A., Grebneva, E.A., Trofimova, O.M., and Antipin, M.Yu., Zh. Strukt. Khim., 2008, vol. 49, no. 2, p. 390.
Korlyukov, A.A., Voronkov, M.G., Zel’bst, E.A., Grebneva, E.A., Trofimova, O.M., Antipin, M.Yu., Zh. Strukt. Khim., 2008, vol. 49, no. 4, p. 760.
Gusev, A.I., Chuklanova, E.B., D’yakov, V.M., Zhdanov, A.S., Alekseev, N.V., Kireeva, L.N., and Kir’yanova, A.N., Dokl. Akad. Nauk SSSR, 1986, vol. 291, no. 3, p. 608.
Bondi, A., J. Phys. Chem., 1964, vol. 68, no. 3, p. 441.
Tamao, K., Hayashi, T., Ito, Y., and Shiro, M., Organometallics, 1992, vol. 11, no. 6, p. 2099.
Day, R., O., Prakasha, T.K., Holmes, R.R., Organometallics, 1994, vol. 13, no. 4, p. 1285.
Kemme, A., Bleidelis, J., Urtane, I., Zelchan, G., and Lukevics, E., J. Organomet. Chem., 1980, vol. 202, no. 2, p. 115.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Andres, J.L., Gonzalez, C., Head-Gordon, M., Replogle, E.S., and Pople, J.A., Gaussian 98, Revision A.6, Gaussian, Pittsburgh PA, 1998.
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Original Russian Text © M.G. Voronkov, O.M. Trofimova, E.A. Grebneva, A.I. Albanov, T.N. Aksamentova, N.N. Chipanina, A.S. Soldatenko, 2010, published in Zhurnal Obshchei Khimii, 2010, Vol. 80, No. 7, pp. 1110–1116.
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Voronkov, M.G., Trofimova, O.M., Grebneva, E.A. et al. New heterosilocanes, 1,1-difluoroand 1-phenyl-1-fluoro-2,8-dioxa-5-chalcogenosilocanes. Russ J Gen Chem 80, 1276–1282 (2010). https://doi.org/10.1134/S1070363210070108
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DOI: https://doi.org/10.1134/S1070363210070108