Skip to main content
Log in

Atranes

XV. The dehydrocondensation of silatrane with alcohols and phenols

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Silatrane,

in the presence of the corresponding sodium alkoxide of phenoxide readily reacts with alcohols and phenols with the liberation of hydrogen and the formation of 1-alkoxy- or 1-aryloxyatranes,

. Depending on the nature of the alcohol or phenol, the rate of the reaction falls in the following sequence: p-CH3OC6H4OH > p-(CH3)3CC6H4OH = n-C4H9OH = = n-C5H11OH > i-C4H9OH > s-C4H9OH > p-CH3C6H4OH > C6H5OH > > p-ClC6H4OH > t-C4H9OH > p-O2NC6H4OH > C6F5OH. The rate of the dehydrocondensation reaction of hydrosilanes with alcohols rises in the sequence

. In the presence of ZnCl2 as catalyst, the dehydrocondensation reaction of silatrane with alcohols takes place considerably more slowly and does not go to completion. The formation of 1-organyloxysilatranes from silatrane and alcohols does not take place in the presence of H2PtCl6 or in the absence of catalysts. Using the dehydrocondensation reaction, twelve 1-organyloxysilatranes have been synthesized, two of which were previously unknown.

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.

Similar content being viewed by others

References

  1. M. G. Voronkov, G. I. Zelchan, V. F. Mironov, Ya. Ya. Bleidelis, and A. A. Kemme, KhGS [Chemistry of Heterocyclic Compounds],4, 227, 1968.

    Google Scholar 

  2. S. Nitzsche, Angew. Chem.63, 490, 1951.

    Google Scholar 

  3. B. N. Dolgov, N. P. Kharitonov, and M. G. Voronkov, ZhOKh,24, 1178, 1954.

    Google Scholar 

  4. V. A. Komarov, V. I. Platonov, N. A. Rodimenkova, N. P. Kharitonov, and Yu. I. Khudobin, ZhFKh,38, 2139, 1964.

    Google Scholar 

  5. E. Ya. Lukevits and M. G. Voronkov, KhGS [Chemistry of Heterocyclic Compounds],1, 171, 1965.

    Google Scholar 

  6. M. E. Havill, I. Joffe, and H. W. Post, J. Org. Chem.,13, 280, 1948.

    Google Scholar 

  7. I. Joffe and H. W. Post, J. Org. Chem.,14, 421, 1949.

    Google Scholar 

  8. A. I. Brodskii and I. G. Khaskin, DAN,74, 299, 1950.

    Google Scholar 

  9. H. Kautsky and E. Daubach, Z. Naturforsch.,5b, 443, 1950.

    Google Scholar 

  10. A. F. Reilly and H. W. Post, J. Org. Chem.,16, 383, 1951.

    Google Scholar 

  11. M. G. Voronkov, The Chemistry of Organosilicon Compounds in the Work of Russian and Soviet Scientists [in Russian], Izd. LGU, Leningrad, pp. 31–32, 1952.

    Google Scholar 

  12. I. G. Khaskin, DAN,85, 129, 1952.

    Google Scholar 

  13. I. G. Khaskin, ZhOKh,23, 32, 1953.

    Google Scholar 

  14. P. Rošciszewski and Z. Sobiczewski, Przem. Chem.,10, 570, 1954.

    Google Scholar 

  15. S. I. Kleshchevnikova, G. A. Dubrovskaya, and E. I. Rumyantseva, Plast. massy, no. 3, 14, 1965.

    Google Scholar 

  16. G. I. Zelchan and M. G. Voronkov, USSR patent no. 192209, 1967; Byull. izobr., no.5, 38, 1967.

  17. G. I. Zelchan and M. G. Voronkov, KhGS Chemistry of Heterocyclic Compounds],3, 371, 1967.

    Google Scholar 

  18. M. G. Voronkov and G. I. Zelchan, Collection: Methods of Preparing Chemical Reagents and Specimens [in Russian], no.14, p. 24, 1966.

    Google Scholar 

  19. M. G. Voronkov, I. B. Mazheika, and G. I. Zelchan, KhGS [Chemistry of Heterocyclic Compounds],1, 58, 1965.

    Google Scholar 

  20. A. N. Egorochkin, V. A. Pestunovich, M. G. Voronkov, and G. I. Zelchan, KhGS [Chemistry of Heterocyclic Compounds],1, 300, 1965.

    Google Scholar 

  21. Yu. P. Egorov, M. G. Voronkov, T. B. Lutsenko, and G. I. Zelchan, KhGS [Chemistry of Heterocyclic Compounds],2, 24, 1966.

    Google Scholar 

  22. M. G. Voronkov, Pure Appl. Chem.,13, 35, 1966.

    Google Scholar 

  23. M. G. Voronkov and G. I. Zelchan, KhGS [Chemistry of Heterocyclic Compounds],1, 210, 1965.

    Google Scholar 

  24. Ya. K. Syrkin, Izv. AN SSSR, OKhN, 389, 401, 1959.

    Google Scholar 

  25. L. Sommer, Stereochemistry, Mechanism, and Silicon [Russian translation], Mir, 1966.

Download references

Author information

Authors and Affiliations

Authors

Additional information

For part XIV, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Voronkov, M.G., Zelchan, G.I. Atranes. Chem Heterocycl Compd 5, 34–38 (1969). https://doi.org/10.1007/BF01031757

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01031757

Keywords

Navigation