Chemistry of Heterocyclic Compounds

, Volume 5, Issue 1, pp 34–38 | Cite as


XV. The dehydrocondensation of silatrane with alcohols and phenols
  • M. G. Voronkov
  • G. I. Zelchan


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.


Hydrogen Sodium Alcohol Phenol Silatrane 
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Copyright information

© Consultants Bureau 1971

Authors and Affiliations

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

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