Skip to main content
Log in

Synthesis of difunctional 1,4-dimethyl-1,4-disilacyclohexanes

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Transformations of HVinSiCl2, HVinSi(Me)Cl, HVinSi(Me)Ph, and HVinSi(Me)NEt2 in the presence of Pt catalyst were studied. In dilute solutions, the reaction gave a mixture of structural and stereoisomers of five- and six-membered disilacyclanes, resulting from intramolecular cyclization of the initially formed linear dimer. In the case of methyl(phenyl)disilacyclane, the structural isomers were separated andtrans-1,4-dimethyl-1,4-diphenyl-1,4-disilacyclohexane was isolated. The reaction of this product with HCl in the presence of AlCl3 followed by hydrolysis resulted in the synthesis oftrans-1,4-dichloro- andtrans-1,4-dihydroxy-1,4-dimethyl-1,4-disilacyclohexanes. The structures of the structural and stereoisomers synthesized were confirmed by1H,13C, and29Si NMR and IR spectroscopies and mass spectrometry.

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. J. W. Curry,J. Am. Chem. Soc., 1956,78, 1686.

    Article  CAS  Google Scholar 

  2. J. W. Curry,J. Org. Chem., 1961,26, 1308.

    Article  CAS  Google Scholar 

  3. K. I. Kobrakov, T. I. Chernysheva, and N. S. Nametkin,Dokl. Akad. Nauk SSSR, 1971,198, 1340 [Dokl. Chem., 1971 (Engl. Transl.)].

    CAS  Google Scholar 

  4. V. M. Vdovin, K. S. Pushchevaya, and A. D. Petrov,Izv. Akad. Nauk SSSR, Ser. Khim., 1961, 281 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1961,10 (Engl. Transl.)].

    Google Scholar 

  5. Yu. A. Egorov, K. S. Pushchevaya, K. D. Lubush, V. M. Vdovin, and A. D. Petrov,Izv. Akad. Nauk SSSR, Ser. Khim., 1963, 822 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1963,12 (Engl. Transl.)].

  6. J. Oklik and J. Bazant,Coll. Czech. Chem. Commun., 1965,30, 2928.

    Google Scholar 

  7. K. I. Kobrakov, L. A. Fedorov, V. V. Kuz'min, N. S. Nametkin, and T. I. Chernysheva,Dokl. Akad. Nauk SSSR, 1970,191, 607 [Dokl. Chem., 1970 (Engl. Transl.)].

    CAS  Google Scholar 

  8. B. Boury, L. Carpender, and R. J. Pelorriu,Angew. Chem., Int. Ed. Engl., 1990,29/7, 785.

    Article  Google Scholar 

  9. B. Boury, R. J. P. Corriu, D. Leclercq, R. H. Matin, J. M. Planeix, and A. Vioux,Organometallics, 1991,10, 1457.

    Article  CAS  Google Scholar 

  10. T. Hoshi, M. Takohashi, and M. Kira,Chem. Lett., 1996, 683.

  11. US Pat. 3,465,019, 1969;RZhKhim. [Chemistry Russ. J. Abstrs.], 1970, 20 H102.

  12. Pol. Pat. 150,116, 1990;Chem. Abstrs., 1991,114, 82110v.

  13. T. V. Astapova, Ph. D. Thesis (Chem.), Institute of Organoelement Compounds, USSR Academy of Sciences, Moscow, 1984, 43 pp. (in Russian).

  14. R. J. P. Corriu, C. Guerin, and J. J. E. Moreau, inThe Chemistry of Organic Silicon Compounds, Eds. S. Patai and Z. Rappoport, J. Wiley and Sons, 1989, 305.

  15. A. R. Bassindale, inThe Chemistry of Organic Silicon Compounds, Eds. S. Patai and Z. Rappoport, J. Wiley and Sons, 1989, 840.

  16. L. H. Sommer and D. F. Bennet,J. Am. Chem. Soc., 1959,81, 251.

    Google Scholar 

  17. N. N. Makarova, B. D. Lavrukhin, and T. V. Timofeeva,Izv. Akad. Nauk SSSR, Ser. Khim. 1985, 443 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985,34 (Engl. Transl.)].

    Google Scholar 

  18. V. A. Ponomarenko, G. V. Odabashchyan and A. D. Petrov,Dokl. Akad. Nauk SSSR, 1960,130, 333, [Dokl. Chem., 1960 (Engl. Transl.)].

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1734–1738, September, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Volkova, L.M., Petrova, I.M., Chizhova, N.V. et al. Synthesis of difunctional 1,4-dimethyl-1,4-disilacyclohexanes. Russ Chem Bull 48, 1712–1716 (1999). https://doi.org/10.1007/BF02494818

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02494818

Key words

Navigation