Skip to main content
Log in

Reaction of Organoelement Hydrides R3EH (E = Si, Ge) with Metal tert-Butylate (M = Al, Ti)-tert-Butyl Hydroperoxide Oxidative Systems

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Lickiss, P.D. and Lucas, R., J. Organomet. Chem., 1995, vol. 521, nos.1–2, p. 229.

    Google Scholar 

  2. Adam, W., Saha-Moller, C.R., and Weichold, O., J. Org. Chem., 2000, vol. 65, no.10, p. 2897.

    Article  PubMed  Google Scholar 

  3. Nagai, Y., Honda, K., and Migita, T., J. Organomet. Chem., 1967, vol. 8, no.3, p. 372.

    Article  Google Scholar 

  4. Anderson, H.H., J. Am. Chem. Soc, 1958, vol. 80, no.19, p. 5083.

    Article  Google Scholar 

  5. Grabovskii, S.A., Cand. Sci. (Chem.) Dissertation, Ufa, 2000.

  6. 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.

  7. Aleksandrov, Yu.A., Zhidkofaznoe okislenie elementoorganichegkikh soedineniy (Liquid-Phase Oxidation of Organoelement Compounds), Moscow: Nauka, 1978.

    Google Scholar 

  8. Shereshovets, V.V., Khursan, S.L., Komissarov, V.D., and, Tolstikov G.A., Usp. Khim., 2001, vol. 70, no.2, p. 123.

    Google Scholar 

  9. Tarunun, B.I., Tarunina, V.N., and Kurskii, Yu.A., Zh. Obshch. Khim., 1998, vol. 58, no.5, p. 1060.

    Google Scholar 

  10. Curtice, J., Gilman, H., and Hammond, G.S., J. Am. Chem. Soc., 1957, vol. 79, no.5, p. 4754.

    Article  Google Scholar 

  11. Johnsom, O.H. and Nebergall, W.H., J. Am. Chem. Soc., 1949, vol. 71, no.5, p. 1720.

    Google Scholar 

  12. Mironov, V.F. and Gar, T.K., Organicheskie soedineniya germaniya (Organogermanium Compounds), Moscow: Nauka, 1967, p. 76.

    Google Scholar 

  13. Spirina, I.V., Maslennikov, V.P., and Aleksandrov, Yu.A., Usp. Khim., 1987, vol. 56, no.7, p. 1167.

    Google Scholar 

  14. 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

    Google Scholar 

  15. 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.

  16. Dodonov, V.A., Stepovik, L.P., Soskova, A.S., and Zaburdaeva, E.A., Zh. Obshch. Khim., 1994, vol. 64, no.10. p. 1715.

    Google Scholar 

  17. Stepovik, L.P., Martynova, I.M., and Dodonov, V.A., Zh. Obshch. Khim., 2000, vol. 70, no.8, p. 1399.

    Google Scholar 

  18. Martynova, I.M., Stepovik, L.P., and Dodonob, V.A., Zh. Obshch. Khim., 2001, vol. 71, no.5, p. 785.

    Google Scholar 

  19. Martynova, I.M., Stepovik, L.P., and Dodonov, V.A., Zh. Obshch. Khim., 2001, vol. 71, no.10, p. 1681.

    Google Scholar 

  20. Stepovik, L.P., Martynova, I.M., and Dodonov, V.A., Zh. Obshch. Khim., 1999, vol. 69, no.2, p. 267.

    Google Scholar 

  21. Zaburdaeva, E.A., Stepovik, L.P., Dodonov, V.A., and Martynova, I.M., Zh. Obshch. Khim., 1997, vol. 67, no.12, p. 2015.

    Google Scholar 

  22. Stepovik, L.P. Zaburdaeva, E.A., and Dodonov, V.A., Zh. Obshch. Khim., 1997, vol. 67, no.2, p. 282.

    Google Scholar 

  23. Stepovik, L.P., Dodonov, V.A., and Zaburdaeva, E.A., Zh. Obshch. Khim., 1997, vol. 67, no.1, p. 116.

    Google Scholar 

  24. Stepovik, L.P., Gulemova, M.V., and Martynova, I.M., Zh. Obshch. Khim., 2005, vol. 75, no.4, p. 545.

    Google Scholar 

  25. Dodonov, V.A., Zaburdaeva, E.A., Stepovik, L.P., and Cherkasov, V.K., Izv. Ross. Akad. Nauk, Ser. Khim., 2003, no. 4, p. 863.

  26. 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.

  27. Emsley, J., The Elements, Oxford: Clarendon, 1989.

    Google Scholar 

  28. Bennet, J.E. and Howard, J.A., J. Am. Chem. Soc., 1972, vol. 94, no.23, p. 8244.

    Article  Google Scholar 

  29. Adeleke, B.B. and Wan, J.K.S., J. Chem. Soc., Perkin Trans. 2, 1980, no. 1, p. 225.

  30. Niki, E., Yokoi, S., Tsuchiya, J., and Kamiya, Y., J. Am. Chem. Soc., 1983, vol. 105, no.6, p. 1498.

    Article  Google Scholar 

  31. Howard, J.A. and Tait, J.C., Can. J. Chem., 1974, vol. 54, no.16, p. 2669.

    Google Scholar 

  32. Sakurai, H., Mochida, K., and Kira, M., J. Organomet. Chem., 1977, vol. 124, no.2, p. 235.

    Article  Google Scholar 

  33. Dodonov, V.A., Stepovik, L.P., and Sofronova, S.M., Zh. Obshch. Khim., 1990, vol. 60, no.8, p. 1839.

    Google Scholar 

  34. Polyanskii, N.G. and Safronenko, E.D., Zh. Prikl. Khim., 1961, vol. 34, no.6, p. 1839.

    Google Scholar 

  35. Bauer, K.H., Die organische Analyse, Leipzig: Geest and Portig, 1954, 3rd ed.

    Google Scholar 

  36. Haslam, J.H., US Patent 2684972, Ref. Zh. Khim., 1955, no. 19, p. 348.

  37. Field, R. and Cowe, P., The Organic Chemistry of Titanium, London: Butterworth, 1965.

    Google Scholar 

  38. Sintezy organicheskikh preparatov (Organic Syntheses), Moscow: Inostrannaya Literatura, 1952, vol. 3, p. 119.

  39. 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.

    Google Scholar 

  40. Dannley, R.L. and Jalics, G., J. Org. Chem., 1965, vol. 30, no.7, p. 2417

    Google Scholar 

  41. Dannley, R.L. and Farrant, G., J. Am. Chem. Soc., 1966, vol. 88, no.3, p. 627.

    Article  Google Scholar 

  42. Rieche, A. and Dahlmann, J., Ann. Chem., 1964, vol. 675, no.13, p. 19.

    Google Scholar 

  43. Houben-Weyl. Metody organicheskoi khimii. Metody analiza. (Houben-Weyl Methods of Organic Chemistry. Methods of Analysis), Moscow: Khimiya, 1967, p. 545.

Download references

Author information

Authors and Affiliations

Authors

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

Reprints 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

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11176-005-0375-y

Keywords

Navigation