Skip to main content
Log in

Chloromethyl(dimethyl)pentafluorophenoxysilane: synthesis and reactions with N-trimethylsilylcarboxamides

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Chloromethyl(dimethyl)pentafluorophenoxysilane (ClCH2SiMe2OC6F5) reacted with trimethylsilyl derivatives of N-methylacetamide, N-phenylacetamide, and N-methylbenzamide to form the corresponding (O—Si) chelates with a pentacoordinated silicon atom: N-[dimethyl(pentafluorophenoxy)silyl]methyl-N-methylacetamide, N-[dimethyl-(pentafluorophenoxy)silyl]methyl-N-phenylacetamide, and N-[dimethyl(pentafluorophenoxy)silyl]methyl-N-methylbenzamide. The structure of products was confirmed by multinuclear NMR spectroscopy, the mechanism of their formation was discussed.

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. R. I. Hillyard, C. M. Ryan, C. H. Yoder, J. Organomet. Chem., 1978, 153, 369; DOI: https://doi.org/10.1016/S0022-328X(00)92060-6.

    Article  CAS  Google Scholar 

  2. C. H. Yoder, C. M. Ryan, G. F. Martin, P. S. Ho, J. Organomet. Chem., 1980, 190, 1; DOI: https://doi.org/10.1016/S0022-328X(00)82874-0.

    Article  CAS  Google Scholar 

  3. M. G. Voronkov, V. A. Pestunovich, Yu. I. Baukov, Organomet. Chem. USSR, 1991, 4, 593.

    Google Scholar 

  4. Yu. I. Baukov, E. P. Kramarova, A. G. Shipov, G. I. Oleneva, O. B. Artamkina, A. I. Albanov, M. G. Voronkov, V. A. Pestunovich, Zh. Obshch. Khim. [Russ. J. Gen. Chem.], 1989, 59, 127 (in Russian).

    CAS  Google Scholar 

  5. V. V. Negrebetsky, Yu.I. Baukov, Russ. Chem. Bull., 1997, 46, 1807; DOI: https://doi.org/10.1007/BF02503766.

    Article  CAS  Google Scholar 

  6. C. Chuit, R. J. P. Corriu, C. Reye, J. C. Young, Chem. Rev., 1993, 93, 1371; DOI: https://doi.org/10.1021/cr00020a003.

    Article  CAS  Google Scholar 

  7. D. Kost, I. Kalikhman, in The Chemistry of Organic Silicon Compounds, Eds Z. Rappoport, Y. Apeloig, Wiley, New York, 1998, p. 1339.

    Chapter  Google Scholar 

  8. O. B. Artamkina, E. P. Kramarova, A. G. Shipov, Yu. I. Baukov, A. A. Macharashvili, Yu. E. Ovchinnikov, Yu. T. Struchkov, Zh. Obshch. Khim. [Russ. J. Gen. Chem.], 1993, 63, 2289 (in Russian).

    CAS  Google Scholar 

  9. I. D. Kalikhman, A. I. Albanov, O. B. Bannikova, L. I. Belousova, M. G. Voronkov, V. A. Pestunovich, A. G. Shipov, E. P. Kramarova, Yu. I. Baukov, J. Organomet. Chem., 1989, 361, 147; DOI: https://doi.org/10.1016/0022-328x(89)85379-3.

    Article  CAS  Google Scholar 

  10. N. F. Lazareva, N. N. Chipanina, L. P. Oznobikhina, B. A. Shainyan, J. Organomet. Chem., 2018, 876, 66; DOI: https://doi.org/10.1016/j.jorganchem.2018.09.007.

    Article  CAS  Google Scholar 

  11. A. R. Bassindale, P. G. Taylor, in The Chemistry of Organic Silicon Compounds, Eds S. Patai, Z. Rappoport, Wiley, Chichester, 1989, Vol. 1, Ch. 13, p. 839.

    Chapter  Google Scholar 

  12. A. R. Bassindale, S. J. Glynn, P. G. Taylor, in The Chemistry of Organic Silicon Compounds, Eds Z. Rappoport, Y. Apeloig, Wiley, Chichester, 1998, Vol. 2, Ch. 9, p. 495.

    Chapter  Google Scholar 

  13. P. Jaramillo, L. R. Domingo, P. Perrez, Chem. Phys. Lett., 2006, 420, 95; DOI:https://doi.org/10.1016/j.cplett.2005.12.047.

    Article  CAS  Google Scholar 

  14. W. A. Sheppard, J. Am. Chem. Soc., 1970, 92, 5419; DOI: https://doi.org/10.1021/ja00721a021.

    Article  CAS  Google Scholar 

  15. M. Matić, N. Bebek, B. Denegri, O. Kronja, Croat. Chem. Acta, 2016, 89, 355; DOI: https://doi.org/10.5562/cca3040.

    Article  Google Scholar 

  16. A. A. Nikolin, A. A. Korlyukov, E. P. Kramarova, D. E. Arkhipov, A. G. Shipov, Yu. I. Baukov, V. V. Negrebetskii, Russ. Chem. Bull., 2019, 68, 1575; DOI: https://doi.org/10.1007/s11172-019-2595-z.

    Article  CAS  Google Scholar 

  17. A. A. Korlyukov, D. E. Arkhipov, A. D. Volodin, V. V. Negrebetskii, A. A. Nikolin, E. P. Kramarova, A. G. Shipov, Yu. I. Baukov, Russ. Chem. Bull., 2019, 68, 137; DOI: https://doi.org/10.1007/s11172-019-2429-z.

    Article  CAS  Google Scholar 

  18. A. D. Shagina, E. P. Kramarova, A. G. Shipov, D. V. Tarasenko, V. V. Negrebetsky, Yu. I. Baukov, Russ. Chem. Bull., 2020, 69, 398; DOI: https://doi.org/10.1007/s11172-020-2775-x.

    Article  CAS  Google Scholar 

  19. A. D. Shagina, E. P. Kramarova, D. V. Tarasenko, D. I. Gonchar, D. N. Lyakhman, A. A. Lagunin, K. A. Sobyanin, T. A. Shmigol’, Yu. I. Baukov, V. V. Negrebetsky, Russ. Chem. Bull., 2021, 70, 479; DOI: https://doi.org/10.1007/s11172-021-3112-8.

    Article  CAS  Google Scholar 

  20. R. Callens, A. Collin, Pat. WO 2012136617 A1 20121011, http://worldwide.espacenet.com/publicationDetails/originalDocument?CC=WO&NR=2012136617A1&KC=A1&FT=D&ND=3&date=20121011&DB=EPODOC&locale=en_EP.

  21. W. L. F. Armarego, C. L. L. Chai, Purification of Laboratory Chemicals, 6th ed., Elsevier, Butterworth-Heinemann, 2009, 752 pp.

  22. G. S. Quiones, G. Hägele, K. Seppelt, Chem. Eur. J., 2004, 10, 4755; DOI: https://doi.org/10.1002/chem.200400095.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. F. Lazareva.

Ethics declarations

The authors declare no competing interests.

Additional information

All results were obtained using the analytical equipment of the Baikal Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 9, pp. 2148–2153, September, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Soldatenko, A.S., Lazareva, N.F. Chloromethyl(dimethyl)pentafluorophenoxysilane: synthesis and reactions with N-trimethylsilylcarboxamides. Russ Chem Bull 72, 2148–2153 (2023). https://doi.org/10.1007/s11172-023-4010-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-4010-z

Key words

Navigation