Abstract
Trialkyl(aryl)silanes and -germanes effectively react with metal (Al, Ti) tert-butylate-tert-butyl-hydroperoxide under mild conditions (room temperature, benzene or tetrachloromethane) mainly by the element-hydrogen bond. The character of the products depends on the nature of the element, the structure of the radical bound to it, and the solvent. The process is radical in nature. It includes the stages of formation of element-centered radicals and their reaction with the oxygen generated by the system. The intermediate organometallic peroxides can also acts as oxidants for the element (Si, Ge)-hydrogen bonds.
Similar content being viewed by others
REFERENCES
Lickiss, P.D. and Lucas, R., J. Organomet. Chem., 1995, vol. 521, nos.1–2, p. 229.
Adam, W., Saha-Moller, C.R., and Weichold, O., J. Org. Chem., 2000, vol. 65, no.10, p. 2897.
Nagai, Y., Honda, K., and Migita, T., J. Organomet. Chem., 1967, vol. 8, no.3, p. 372.
Anderson, H.H., J. Am. Chem. Soc, 1958, vol. 80, no.19, p. 5083.
Grabovskii, S.A., Cand. Sci. (Chem.) Dissertation, Ufa, 2000.
Grabovskii, S.A., Ivanova, I.V., and Kabal’nova, N.N., Abstracts of Papers, Vserossiiskii simpozium “Khimiya organicheskikh soedinenii kremniya i sery” (Russian Symp. “Chemistry of the Organic Compounds of Silicon and Sulfur”), Irkutsk, 2001, p. 198.
Aleksandrov, Yu.A., Zhidkofaznoe okislenie elementoorganichegkikh soedineniy (Liquid-Phase Oxidation of Organoelement Compounds), Moscow: Nauka, 1978.
Shereshovets, V.V., Khursan, S.L., Komissarov, V.D., and, Tolstikov G.A., Usp. Khim., 2001, vol. 70, no.2, p. 123.
Tarunun, B.I., Tarunina, V.N., and Kurskii, Yu.A., Zh. Obshch. Khim., 1998, vol. 58, no.5, p. 1060.
Curtice, J., Gilman, H., and Hammond, G.S., J. Am. Chem. Soc., 1957, vol. 79, no.5, p. 4754.
Johnsom, O.H. and Nebergall, W.H., J. Am. Chem. Soc., 1949, vol. 71, no.5, p. 1720.
Mironov, V.F. and Gar, T.K., Organicheskie soedineniya germaniya (Organogermanium Compounds), Moscow: Nauka, 1967, p. 76.
Spirina, I.V., Maslennikov, V.P., and Aleksandrov, Yu.A., Usp. Khim., 1987, vol. 56, no.7, p. 1167.
Stepovik, L.P., Martynova, I.M., Dodonov, V.A., and Cherkasov, V.K., Izv. Ross. Akad. Nauk, Ser. Khim., 2002, vol. 51, no.4, p. 590
Stepovik, L.P., Dodonov, V.A., Gulenova, M.V., Martynova, I.M., and Cherkasov, V.K., Abstracts of Papers, XI Mezhdunarodnya konferentsiya po khimii organicheskikh i elementorganicheskikh soedinenii (XI Int. Conf. on the Chemistry of Organic and Organoelement Peroxides), Moscow, 2003, p. 25.
Dodonov, V.A., Stepovik, L.P., Soskova, A.S., and Zaburdaeva, E.A., Zh. Obshch. Khim., 1994, vol. 64, no.10. p. 1715.
Stepovik, L.P., Martynova, I.M., and Dodonov, V.A., Zh. Obshch. Khim., 2000, vol. 70, no.8, p. 1399.
Martynova, I.M., Stepovik, L.P., and Dodonob, V.A., Zh. Obshch. Khim., 2001, vol. 71, no.5, p. 785.
Martynova, I.M., Stepovik, L.P., and Dodonov, V.A., Zh. Obshch. Khim., 2001, vol. 71, no.10, p. 1681.
Stepovik, L.P., Martynova, I.M., and Dodonov, V.A., Zh. Obshch. Khim., 1999, vol. 69, no.2, p. 267.
Zaburdaeva, E.A., Stepovik, L.P., Dodonov, V.A., and Martynova, I.M., Zh. Obshch. Khim., 1997, vol. 67, no.12, p. 2015.
Stepovik, L.P. Zaburdaeva, E.A., and Dodonov, V.A., Zh. Obshch. Khim., 1997, vol. 67, no.2, p. 282.
Stepovik, L.P., Dodonov, V.A., and Zaburdaeva, E.A., Zh. Obshch. Khim., 1997, vol. 67, no.1, p. 116.
Stepovik, L.P., Gulemova, M.V., and Martynova, I.M., Zh. Obshch. Khim., 2005, vol. 75, no.4, p. 545.
Dodonov, V.A., Zaburdaeva, E.A., Stepovik, L.P., and Cherkasov, V.K., Izv. Ross. Akad. Nauk, Ser. Khim., 2003, no. 4, p. 863.
Zaburdaeva, E.A., Dodonov, V.A., and Stepovik, L.P., Abstracts of Papers, Tret’ya molodezhnaya shkola-konferentsiya po organicheskomu sintezu “Organicheskii sintez v novom stolenii” (Third Junior School-Conf. on Organic Synthesis “Organic Synthesis in the New Century”), St. Petersburg, 2002, p. 184.
Emsley, J., The Elements, Oxford: Clarendon, 1989.
Bennet, J.E. and Howard, J.A., J. Am. Chem. Soc., 1972, vol. 94, no.23, p. 8244.
Adeleke, B.B. and Wan, J.K.S., J. Chem. Soc., Perkin Trans. 2, 1980, no. 1, p. 225.
Niki, E., Yokoi, S., Tsuchiya, J., and Kamiya, Y., J. Am. Chem. Soc., 1983, vol. 105, no.6, p. 1498.
Howard, J.A. and Tait, J.C., Can. J. Chem., 1974, vol. 54, no.16, p. 2669.
Sakurai, H., Mochida, K., and Kira, M., J. Organomet. Chem., 1977, vol. 124, no.2, p. 235.
Dodonov, V.A., Stepovik, L.P., and Sofronova, S.M., Zh. Obshch. Khim., 1990, vol. 60, no.8, p. 1839.
Polyanskii, N.G. and Safronenko, E.D., Zh. Prikl. Khim., 1961, vol. 34, no.6, p. 1839.
Bauer, K.H., Die organische Analyse, Leipzig: Geest and Portig, 1954, 3rd ed.
Haslam, J.H., US Patent 2684972, Ref. Zh. Khim., 1955, no. 19, p. 348.
Field, R. and Cowe, P., The Organic Chemistry of Titanium, London: Butterworth, 1965.
Sintezy organicheskikh preparatov (Organic Syntheses), Moscow: Inostrannaya Literatura, 1952, vol. 3, p. 119.
Kocheshkov, K.A., Zemlyanskii, N.N., Sheverdina, N.I., and Panov, E.M., Metody elementoorganicheskoi khimii. Germanii, olovo, svinets (Methods of Orgamoelement Chemistry. Germanium, Tin, Lead), Moscow: Nauka, 1968, p. 124.
Dannley, R.L. and Jalics, G., J. Org. Chem., 1965, vol. 30, no.7, p. 2417
Dannley, R.L. and Farrant, G., J. Am. Chem. Soc., 1966, vol. 88, no.3, p. 627.
Rieche, A. and Dahlmann, J., Ann. Chem., 1964, vol. 675, no.13, p. 19.
Houben-Weyl. Metody organicheskoi khimii. Metody analiza. (Houben-Weyl Methods of Organic Chemistry. Methods of Analysis), Moscow: Khimiya, 1967, p. 545.
Author information
Authors and Affiliations
Additional information
__________
Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 7, 2005, pp. 1161–1170.
Original Russian Text Copyright © 2005 by Stepovik, Gulenova, Martynova, Skvortsov, Cherkasov.
Rights and permissions
About this article
Cite this article
Stepovik, L.P., Gulenova, M.V., Martynova, I.M. et al. Reaction of Organoelement Hydrides R3EH (E = Si, Ge) with Metal tert-Butylate (M = Al, Ti)-tert-Butyl Hydroperoxide Oxidative Systems. Russ J Gen Chem 75, 1098–1107 (2005). https://doi.org/10.1007/s11176-005-0375-y
Received:
Issue Date:
DOI: https://doi.org/10.1007/s11176-005-0375-y