Skip to main content
SpringerLink
Log in

Atranes. I. A new method for synthesizing 1-alkyl and aryl silatranes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A new simple method for synthesizing organyl(2, 2′, 2″-aminotriethoxy)silanes R

, named 1-organylsilatranes, is developed. It is based on splitting polyorganylsesquisiloxanes (RSiO1.5)x, polyorganylsiloxanols [RSiO1, 5−y(OH)2y]x, or polyorganylhydrosiloxanes (RSiHO)m with triethanolamine in the presence of an alkaline catalyst. Six compounds of the type mentioned were synthesized by this method, of which three (1-ethyl-, 1-isopropyl- and 3, 7-dimethyl-1-phenylsilatrane) were previously unknown, and certain of their properties are described. The resistance of 1-organylsilatranes to hydrolysis, their high dipole moments, and their inability to give ammonium compounds when treated with CH3I indicate that they contain an intramolecular coordinated link Si←N. 1-Arylsilatranes have a well-defined physiological activity.

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. S. A. Rojahn, German Pat. 582149 (1933); C., II, 2704, 1933.

  2. Y. Hirata, K. Inukai, T. Tsujiuchi, J. Chem. Soc. Japan, Pure Chem. Sect., 69, 58, 1948.

    Google Scholar 

  3. H. C. Brown, E. A. Fletcher, J. Am. Chem. Soc., 73, 2808, 1951.

    Google Scholar 

  4. Fr. Hein, R. Burkchardt, Z. anorg. Chem., 268, 159, 1952.

    Google Scholar 

  5. C. A. Lucchesi, Diss. Abstr., 15, 2007, 1955.

    Google Scholar 

  6. S. H. Langer, I. N. Elbling, Ind. Eng. Chem., 49, 1113, 1957.

    Google Scholar 

  7. I. N. Elbing, S. H. Langer, U.S. Pat. 2, 785, 192 (1957); C. A., 51, 11377, 1957.

    Google Scholar 

  8. H. Steinberg, D. L. Hunter, Ind. Eng. Chem., 49, 174, 1957.

    Google Scholar 

  9. H. Weidmann, H. K. Zimmerman, Ann., 619, 28, 1958.

    Google Scholar 

  10. H. Weidmann, H. K. Zimmerman, Ann., 620, 4, 1959.

    Google Scholar 

  11. H. K. Zimmerman, H. Weidmann, Ann., 628, 37, 1959.

    Google Scholar 

  12. H. Steinberg, D. L. Hunter. J. Am. Chem. Soc., 82, 853, 1960.

    Google Scholar 

  13. A. A. Schleppnik, C. D. Gutsche, J. Org. Chem., 25, 1378, 1960.

    Google Scholar 

  14. R. Neu, Arch. Pharmazie, 294/66, 721, 1961.

    Google Scholar 

  15. A. A. Schleppnik, C. D. Gutsche, J. Org. Chem., 27, 3684, 1962.

    Google Scholar 

  16. Fr. Hein, P. W. Albert, Z. anorg. Chem., 269, 67, 1952.

    Google Scholar 

  17. S. G. Kemp, V. G. Bashford, Brit. Pat. 810, 323 (1959); C. A., 53, 12741, 1959.

    Google Scholar 

  18. A. B. Finestone, U.S. Pat 2, 953, 545 (1960); C. A., 55, 4045, 1961; German Pat. 1, 131, 681 (1962); C. A., 58, 4598, 1963.

    Google Scholar 

  19. C. L. Frye, G. E. Vogel, J. A. Hall, J. Am. Chem. Soc., 83, 996, 1961.

    Google Scholar 

  20. Wm. T. Miller, J. Am. Chem. Soc., 62, 2707, 1940.

    Google Scholar 

  21. K. Starke, J. Inorg. Nucl. Chem., 6, 130, 1958.

    Google Scholar 

  22. F. C. Burns, K. Starke, Trans. Kentucky Acad. Sci., 19, 45, 1958.

    Google Scholar 

  23. K. Starke, J. Inorg. Nucl, Chem., 11, 37, 1959.

    Google Scholar 

  24. K. Starke, Trans. Kentucky Acad. Sci., 20, 41, 1959.

    Google Scholar 

  25. M. G. Voronkov, G. I. Zelchan, USSR Pat. 162139 (1964).

  26. M. G. Voronkov, Izv. AN SSSR, OKhN, 882, 1957; ZhOKh, 29, 1528, 1959.

  27. Ya. Ya. Baltkais, M. G. Voronkov, G. I. Zelchan, Izv. AN Latv. SSR, no. 2, 102, 1964.

    Google Scholar 

  28. R. O. Sauer, W. J. Scheiber, S. D. Brewer, J. Am. Chem, Soc., 68, 962, 1946.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Synthesis AS Latvian SSR, Riga

    M. G. Voronkov & G. I. Zelchan

Authors
  1. M. G. Voronkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. I. Zelchan
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Voronkov, M.G., Zelchan, G.I. Atranes. I. A new method for synthesizing 1-alkyl and aryl silatranes. Chem Heterocycl Compd 1, 33–37 (1965). https://doi.org/10.1007/BF01168915

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01168915

Keywords

Search

Navigation