Skip to main content
SpringerLink
Log in

1-Organyl-2-azasilatran-3-ones

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

Abstract

New 1-organyl-2-azasilatran-3-ones have been synthesized via the reaction of trifunctional silanes RSiX3 (R = Et, Pr, Ph, CH2=CH, or ClCH2; X = Cl or Me2N) with N,N-bis(2-hydroxyethyl)glycinamides (HOCH2CH2)2NCH2C(O)NHR (R = H or Me) and their N′,O-trimethylsilyl derivatives. The obtained products can be hydrolyzed to give the corresponding organylsilanetriols. Lithiation of 1-methyl- and 1-phenyl-2-azasilatran-3-ones with n-butyllithium or their reduction with lithium aluminum hydride leads to the products of splitting of the atrane backbone RSiBu3 and RSiH3 (R = Me or Ph), respectively.

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

Access this article

Log in via an institution

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. Frye, C.L., Vogel, G.E., and Hall, J.A., J. Am. Chem. Soc., 1961, vol. 83, no. 4, p. 996.

    Article  CAS  Google Scholar 

  2. Voronkov, M.G., Dyakov, V.M., and Kirpichenko, S.V., J. Organomet. Chem., 1982, vol. 233, no. 1, p. 1.

    Article  CAS  Google Scholar 

  3. Verkade, J.G., Coord. Chem. Rev., 1994, vol. 137, p. 233.

    Article  CAS  Google Scholar 

  4. The Chemistry of Organic Silicon Compounds, Rappoport, Z. and Apeloig, Y., Eds., New York: John Wiley & Sons Ltd., 1998, vol. 2, ch. 24, p. 1539.

    Google Scholar 

  5. Puri, J.K., Singh, R., and Chahal, V.K., Chem. Soc. Rev., 2011, vol. 40, no. 3, p. 1791.

    Article  CAS  Google Scholar 

  6. Mazeika, I., Grinberga, S., Gaukhman, A.P., Zelchan, G.I., and Lukevics, E., J. Organometal. Chem., 1992, vol. 426, p. 41.

    Article  CAS  Google Scholar 

  7. Pestunovich, V.A., Lazareva, N.F., Kozyreva, O.B., Klyba, L.V., Gavrilova, G.A., and Voronkov, M.G., Russ. J. Gen. Chem., 1998, vol. 68, no. 1, p. 44.

    CAS  Google Scholar 

  8. Lazareva, N.F., Pestunovich, V.A., Albanov, A.I., Vesnin, M.G., and Voronkov, M.G., Tetrahedron Lett., 2000, vol. 41, no. 24, p. 4823.

    Article  CAS  Google Scholar 

  9. Pestunovich, V.A., Lazareva, N.F., Albanov, A.I., Buravtseva, E.N., and Gusel’nikov, L.E., Russ. J. Gen. Chem., 2006, 76, no. 6, p. 931.

    Article  CAS  Google Scholar 

  10. Popowski, E., Michalik, M., and Kelling, H., J. Organomet. Chem., 1975, vol. 88, no. 2, p. 157.

    Article  CAS  Google Scholar 

  11. Takiguchi, T., J. Am. Chem. Soc., 1959, vol. 81, no. 10, p. 2359.

    Article  CAS  Google Scholar 

  12. Murugavel, R., Chandrasekhar, V., and Roesky, H.W., Acc. Chem. Res., 1996, vol. 29, no. 4, p. 183.

    Article  CAS  Google Scholar 

  13. Murugavel, R., Voigt A., Walawalkar, M.G., and Roesky, H.W., Chem. Rev., 1996, vol. 96, no. 6, p. 2205.

    Article  CAS  Google Scholar 

  14. Chandrasekhar, V., Boomishankar, R., and Nagendran, S., Chem. Rev., 2004, vol. 104, no. 12, p. 5847.

    Article  CAS  Google Scholar 

  15. Murugavel, R., Bhattacharjee, M., and Roesky, H.W., Appl. Organometal. Chem., 1999, vol. 13, no. 4, p. 227.

    Article  CAS  Google Scholar 

  16. Ishida, H., Koenig, J.L., and Gardner, K.C., J. Chem. Phys., 1982, vol. 77, no. 11, p. 5748.

    Article  CAS  Google Scholar 

  17. Cerveau, G., Chuit, C., Corriu, R.J.P., Nayyar, N.K., and Reye, C., J. Organomet. Chem., 1990, vol. 389, no. 2, p. 159.

    Article  CAS  Google Scholar 

  18. Gordon, A.J. and Ford, R.A., The Chemist’s Companion. A Handbook of Practical Data, Techniques and References, New York: Wiley, 1972.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A.E. Favorskii Irkutsk Institute of Chemistry, Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    N. F. Lazareva & I. M. Lazarev

Authors
  1. N. F. Lazareva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. M. Lazarev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. F. Lazareva.

Additional information

Original Russian Text © N.F. Lazareva, I.M. Lazarev, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 9, pp. 1426–1433.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lazareva, N.F., Lazarev, I.M. 1-Organyl-2-azasilatran-3-ones. Russ J Gen Chem 83, 1652–1659 (2013). https://doi.org/10.1134/S1070363213090053

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363213090053

Keywords

Search

Navigation