Skip to main content
SpringerLink
Log in

Acyl iodides in organic synthesis: IX. Cleavage of the Si-O-C and Si-O-Si moieties

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

Abstract

Reactions of acyl iodides RCOI (R = Me, Ph) with organosilicon compounds involve cleavage of the Si-O-C and Si-O-Si fragments. Acetyl iodide reacts with alkyl(alkoxy)silanes with evolution of heat, and cleavage of the Si-O bond results in the formation of oligo-or polysiloxanes, alkyl iodides, and alkyl acetates. 1,3-Diacetoxytetramethyldisiloxane is formed in the reaction of acetyl iodide with dimethoxy(dimethyl)silane. Acyl iodides readily react with 1-ethoxysilatrane to give 1-acyloxysilatranes as a result of cleavage of the C-O bond. The reaction of acetyl iodide with hexaethyldisiloxane yields triethylsilyl acetate and triethyliodosilane, while in the reaction with octamethyltrisiloxane iodo(trimethyl)silane and dimethyl(trimethylsiloxy)silyl acetate are obtained.

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. Voronkov, M.G. and Basenko, S.V., Sov. Sci. Rev., 1990, vol. 15, p. 1.

    Google Scholar 

  2. Voronkov, M.G. and Khudobin, A.Yu., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1956, no. 6, p. 713.

  3. Voronkov, M.G., Pavlov, S.F., and Dubinskaya, E.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1975, no. 3, p. 657.

  4. Voronkov, M.G., Pavlov, S.F., and Dubinskaya, E.I., Dokl. Akad. Nauk SSSR, 1976, vol. 227, p. 607.

    CAS  Google Scholar 

  5. Voronkov, M.G., Dubinskaya, E.I., and Chuikova, N.A., Zh. Obshch. Khim., 1977, vol. 47, p. 2335.

    Google Scholar 

  6. Voronkov, M.G., Brodskaya, E.I., Keiko, V.V., Shevchenko, S.G., Bazhenova, T.N., Pavlov, S.F., Modonov, V.B., Dubinskaya, E.I., and Frolov, Yu.L., Dokl. Akad. Nauk SSSR, 1977, vol. 232, p. 1100.

    CAS  Google Scholar 

  7. Voronkov, M.G. and Chudesova, L.M., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1957, no. 11, p. 1415.

  8. Voronkov, M.G. and Chudesova, L.M., Zh. Obshch. Khim., 1959, vol. 29, p. 1534.

    CAS  Google Scholar 

  9. Voronkov, M.G. and Sviridova, N.G., Usp. Khim., 1971, vol. 40, p. 1761.

    CAS  Google Scholar 

  10. Voronkov, M.G., Mileshkevich, V.P., and Yuzhelevskii, Yu.A., Siloxanovaya svyaz’ (The Siloxane Bond), Novosibirsk: Nauka, 1976, p. 231.

    Google Scholar 

  11. Voronkov, M.G., Mileshkevich, V.P., and Yuzhelevskii, Yu.A., The Siloxane Bond: Physical Properties and Chemical Transformations, New York: Consultants Bureau, 1978.

    Google Scholar 

  12. Post, G.R., J. Org. Chem., 1942, vol. 7, p. 528.

    Article  CAS  Google Scholar 

  13. Voronkov, M.G., Vlasova, N.N., and Trukhina, A.A., Sovremennyi organicheskii sintez (Contemporary Organic Synthesis), Moscow: Khimiya-Reaktiv, 2003, p. 9.

    Google Scholar 

  14. Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Russ. J. Org. Chem., 2002, vol. 38, p. 1576.

    Article  CAS  Google Scholar 

  15. Voronkov, M.G. and Shagun, V.A., Russ. J. Org. Chem., 2003, vol. 39, p. 331.

    Article  Google Scholar 

  16. Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Russ. J. Org. Chem., 2002, vol. 38, p. 1579.

    Article  CAS  Google Scholar 

  17. Voronkov, M.G., Belousova, L.I., Trukhina, A.A., and Vlasova, N.N., Russ. J. Org. Chem., 2003, vol. 39, p. 1702.

    Article  CAS  Google Scholar 

  18. Voronkov, M.G. and Zelchan, G.I., USSR Inventor’s Certificate no. 242171, 1969; Byull. Izobret., 1969, no. 25.

  19. Voronkov, M.G., Dyakov, V.M., and Kirpichenko, S.V., J. Organomet. Chem., 1982, vol. 233, p. 1.

    Article  CAS  Google Scholar 

  20. Frye, C.L., Vincent, G.A., and Finzel, W.A., J. Am. Chem. Soc., 1971, vol. 93, p. 6805.

    Article  CAS  Google Scholar 

  21. Voronkov, M.G., Baryshok, V.P., Petukhov, L.P., Rakhlin, V.I., Mirskov, R.G., and Pestunovich, V.A., J. Organomet. Chem., 1988, vol. 358, p. 39.

    Article  CAS  Google Scholar 

  22. Ashby, B.A., UK patent no. 990657, 1965; Chem. Abstr., 1965, vol. 63, p. 3076.

  23. Borisov, S.N., Voronkov, M.G., and Sviridova, N.G., Zh. Obshch. Khim., 1969, vol. 39, p. 559.

    CAS  Google Scholar 

  24. Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Russ. J. Org. Chem., 2004, vol. 40, p. 357.

    Article  CAS  Google Scholar 

  25. Teobald, D.W. and Smith, J.C., Chem. Ind., 1958, vol. 32, p. 1007.

    Google Scholar 

  26. Simon, A. and Arnold, H., J. Prakt. Chem., 1959, vol. 8, p. 241.

    Article  CAS  Google Scholar 

  27. Spravochnik khimika (Chemist’s Handbook), Nikol’skii, B.P., Ed., Moscow: Khimiya, 1963, vol. 2, p. 398.

    Google Scholar 

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

    M. G. Voronkov, A. A. Trukhina, L. I. Belousova, G. A. Kuznetsova & N. N. Vlasova

Authors
  1. M. G. Voronkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Trukhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. I. Belousova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. A. Kuznetsova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. N. Vlasova
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Original Russian Text © M.G. Voronkov, A.A. Trukhina, L.I. Belousova, G.A. Kuznetsova, N.N. Vlasova, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 4, pp. 505–509.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Voronkov, M.G., Trukhina, A.A., Belousova, L.I. et al. Acyl iodides in organic synthesis: IX. Cleavage of the Si-O-C and Si-O-Si moieties. Russ J Org Chem 43, 501–506 (2007). https://doi.org/10.1134/S1070428007040021

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428007040021

Keywords

Search

Navigation