Skip to main content
SpringerLink
Log in

Synthesis of 3,3-Dialkoxy-2-trialkylsiloxypropenes

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Silylation of 1,1-dialkoxy-2-propanones with trimethyl- and tert-butyldimethylsilyl chlorides and trifluoromethanesulfonates in the presence of triethylamine and/or 1,8-diazabicyclo[5.4.0]undec-7-ene in various solvents leads to 2-trialkylsiloxypropenal acetals in up to 60% yield.

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. Hoffman, H.M.R., Angew. Chem., 1973, vol. 12, p. 819.

    Google Scholar 

  2. Mann, J., Tetrahedron, 1986, vol. 42, p. 4611.

    Google Scholar 

  3. Lee, J.C., Jin, S., and Cha, J.K., J. Org. Chem., 1998, vol. 63, p. 2804.

    Google Scholar 

  4. Fohlisch, B., Krimmer, D., Gehrlach, E., and Kashammer, D., Chem. Ber., 1988, vol. 121, p. 1585.

    Google Scholar 

  5. Murray, D.H. and Albizati, K.F., Tetrahedron Lett., 1990, vol. 31, no. 29, p. 4109.

    Google Scholar 

  6. Pierau, S. and Hoffmann, H.M.R., Synlett, 1999, no. 2, p. 213.

  7. Stark, B.W., Pierau, S., Wartchow, R., and Hoffmann, H.M.R., Chem. Eur. J., 2000, vol. 6, p. 684.

    Google Scholar 

  8. Keiko, N.A. and Voronkov, M.G., Zh. Vses. Khim. Ob-va., 1991, vol. 36, p. 468.

    Google Scholar 

  9. Keiko, N.A., Rulev, A.Yu., Kalikhman, I.D., and Voronkov, M.G., Izv. Akad. Nauk SSSR, Ser. Khim., 1984, p. 1878.

  10. Taniguchi, Y., Inanaga, J., and Yamaguchi, M. Bull. Chem. Soc. Jpn., 1981, vol. 54, p. 3229.

    Google Scholar 

  11. Emde, H., Domsch, D., Feger, H., Frick, U., Götz, A., Hergoff, H.H., Hoffmann, K., Kober, W., Krägeloh, K., Oesterle, T. Steppan, W., West, W., and Simchen, G., Synthesis, 1982, p. 1; Brownbridge, P., Synthesis, 1983, p. 1; Voronkov, M.G., Maletina, E.A., and Roman, V.K., Kremnekislorodnye soedineniya nemetallov. Proizvodnye kisloroda i sery (Silicon-Oxygen Nonmetal Compounds. Derivatives of Oxygen and Sulfur), Novosibirsk: Nauka, 1991, p. 154.

  12. House, H.O., Czuba, L.J., Gall, M., and Olmstread, H.D., J. Org. Chem., 1969, vol. 34, p. 2324.

    Google Scholar 

  13. Chaudhary, S.K. and Hernandez, O., Tetrahedron Lett., 1979, p. 99.

  14. Bassindale, A.R. and Stout, T., Tetrahedron Lett., 1985, vol. 26, p. 3403.

    Google Scholar 

  15. Emde, H. and Simchen, G., Justus Liebigs Ann. Chem., 1981, p. 1643.

  16. Emde, H. and Simchen, G., Synthesis, 1977, p. 636; Ardecky, R.J., Kerdecky, F.A.J., and Cava, M.P., J. Org. Chem., 1981, vol. 46, p. 1483; Colvin, E.W., Silicon Reagents in Organic Synthesis, London: Academic, 1988, p. 100.

  17. Brownbridge, P. and Chang, T.H., Tetrahedron Lett., 1980, vol. 21, p. 3423.

    Google Scholar 

  18. Hergott, H.H. and Simchen, G., Justus Liebigs Ann. Chem., 1980, p. 1718.

  19. Aizpurua, J.M. and Palomo, C., Tetrahedron Lett., 1985, vol. 26, p. 475.

    Google Scholar 

  20. Ogilvie, K.K. and Iwacha, D.J., Tetrahedron Lett., 1973, p. 317.

  21. Corey, E.J. and Venkateswarlu, A., J. Am. Chem. Soc., 1972, vol. 94, p. 6190.

    Google Scholar 

  22. Corey, E.J., Cho, H., Rücher, C., and Hua, D.H., Tetrahedron Lett., 1981, vol. 22, p. 3455.

    Google Scholar 

  23. Murai, S., Ryu, I., Kadono, Y., and Katayama, H., Chem. Lett., 1977, p. 1219; Creary, X., Inocencio, P.A., Underiner, T.L., and Kostromin, R., J. Org. Chem., 1985, vol. 50, p. 1932.

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    N. A. Keiko, T. A. Kuznetsova, Yu. A. Chuvashev, L. V. Sherstyannikova, L. I. Larina & M. G. Voronkov

Authors
  1. N. A. Keiko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. A. Kuznetsova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. A. Chuvashev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. L. V. Sherstyannikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. I. Larina
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. M. G. Voronkov
    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

Keiko, N.A., Kuznetsova, T.A., Chuvashev, Y.A. et al. Synthesis of 3,3-Dialkoxy-2-trialkylsiloxypropenes. Russian Journal of Organic Chemistry 39, 1393–1397 (2003). https://doi.org/10.1023/B:RUJO.0000010552.72828.63

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUJO.0000010552.72828.63

Keywords

Search

Navigation