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Chemistry of Heterocyclic Compounds

, Volume 1, Issue 1, pp 33–37 | Cite as

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

  • M. G. Voronkov
  • G. I. Zelchan
Article

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.

Keywords

Ammonium Hydrolysis Silane Organic Chemistry Dipole Moment 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    S. A. Rojahn, German Pat. 582149 (1933); C., II, 2704, 1933.Google Scholar
  2. 2.
    Y. Hirata, K. Inukai, T. Tsujiuchi, J. Chem. Soc. Japan, Pure Chem. Sect., 69, 58, 1948.Google Scholar
  3. 3.
    H. C. Brown, E. A. Fletcher, J. Am. Chem. Soc., 73, 2808, 1951.Google Scholar
  4. 4.
    Fr. Hein, R. Burkchardt, Z. anorg. Chem., 268, 159, 1952.Google Scholar
  5. 5.
    C. A. Lucchesi, Diss. Abstr., 15, 2007, 1955.Google Scholar
  6. 6.
    S. H. Langer, I. N. Elbling, Ind. Eng. Chem., 49, 1113, 1957.Google Scholar
  7. 7.
    I. N. Elbing, S. H. Langer, U.S. Pat. 2, 785, 192 (1957); C. A., 51, 11377, 1957.Google Scholar
  8. 8.
    H. Steinberg, D. L. Hunter, Ind. Eng. Chem., 49, 174, 1957.Google Scholar
  9. 9.
    H. Weidmann, H. K. Zimmerman, Ann., 619, 28, 1958.Google Scholar
  10. 10.
    H. Weidmann, H. K. Zimmerman, Ann., 620, 4, 1959.Google Scholar
  11. 11.
    H. K. Zimmerman, H. Weidmann, Ann., 628, 37, 1959.Google Scholar
  12. 12.
    H. Steinberg, D. L. Hunter. J. Am. Chem. Soc., 82, 853, 1960.Google Scholar
  13. 13.
    A. A. Schleppnik, C. D. Gutsche, J. Org. Chem., 25, 1378, 1960.Google Scholar
  14. 14.
    R. Neu, Arch. Pharmazie, 294/66, 721, 1961.Google Scholar
  15. 15.
    A. A. Schleppnik, C. D. Gutsche, J. Org. Chem., 27, 3684, 1962.Google Scholar
  16. 16.
    Fr. Hein, P. W. Albert, Z. anorg. Chem., 269, 67, 1952.Google Scholar
  17. 17.
    S. G. Kemp, V. G. Bashford, Brit. Pat. 810, 323 (1959); C. A., 53, 12741, 1959.Google Scholar
  18. 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. 19.
    C. L. Frye, G. E. Vogel, J. A. Hall, J. Am. Chem. Soc., 83, 996, 1961.Google Scholar
  20. 20.
    Wm. T. Miller, J. Am. Chem. Soc., 62, 2707, 1940.Google Scholar
  21. 21.
    K. Starke, J. Inorg. Nucl. Chem., 6, 130, 1958.Google Scholar
  22. 22.
    F. C. Burns, K. Starke, Trans. Kentucky Acad. Sci., 19, 45, 1958.Google Scholar
  23. 23.
    K. Starke, J. Inorg. Nucl, Chem., 11, 37, 1959.Google Scholar
  24. 24.
    K. Starke, Trans. Kentucky Acad. Sci., 20, 41, 1959.Google Scholar
  25. 25.
    M. G. Voronkov, G. I. Zelchan, USSR Pat. 162139 (1964).Google Scholar
  26. 26.
    M. G. Voronkov, Izv. AN SSSR, OKhN, 882, 1957; ZhOKh, 29, 1528, 1959.Google Scholar
  27. 27.
    Ya. Ya. Baltkais, M. G. Voronkov, G. I. Zelchan, Izv. AN Latv. SSR, no. 2, 102, 1964.Google Scholar
  28. 28.
    R. O. Sauer, W. J. Scheiber, S. D. Brewer, J. Am. Chem, Soc., 68, 962, 1946.Google Scholar

Copyright information

© The Faraday Press, Inc. 1965

Authors and Affiliations

  • M. G. Voronkov
    • 1
  • G. I. Zelchan
    • 1
  1. 1.Institute of Organic Synthesis AS Latvian SSRRiga

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