Skip to main content
Log in

Synthesis of functionalized trimethylsilyl aminomethylphosphinates containing triethoxysilyl moieties

  • Brief Communications
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A convenient synthesis of functionalized trimethylsilyl aminomethylphosphinates containing triethoxysilyl moieties was developed. Radical addition of bis(trimethylsiloxy)-phosphine to triethoxy(vinyl)silane proceeds regioselectively to afford a novel synthon, (2-triethoxysilylethyl)phosphonite, subsequent aminomethylation of which gives the target phosphinates.

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.

References

  1. V. P. Kukhar, H. R. Hudson, Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity, Wiley, New York, USA, 2000, 634.

    Google Scholar 

  2. S. C. Fields, Tetrahedron, 1999, 55, 12237.

    Article  CAS  Google Scholar 

  3. O. I. Kolodiazhnyi, Russ. Chem. Rev., 2006, 75, 227; DOI: https://doi.org/10.1070/RC2006v075n03ABEH001193.

    Article  CAS  Google Scholar 

  4. B. Stowasser, K.-H. Budt, L. Jian-Qi, A. Peyman, D. Ruppert, Tetrahedron Lett., 1992, 33, 6625.

    Article  CAS  Google Scholar 

  5. M. I. Kabachnik, Yu. B. Shalnev, V. K. Promonenkov, L. V. Kovalenko, T. A. Mastryukova, I. L. Odinets, Methods for the Preparation and Biological Activity of Phosphinothricin and Its Derivatives. Results of Science and Technology. Organic Chemistry, VINITI AS USSR, Moscow, 1988, 8, 110 (in Russian).

    Google Scholar 

  6. M. G. Voronkov, V. M. Dyakov, Silatranes, Nauka, Novosibirsk, 1978, 208 (in Russian).

    Google Scholar 

  7. C. A. Black, J. W. Ucci, J. S. Vorpagel, M. C. Mauck, E. E. Fenlon, Bioorganic Medicinal Chem. Lett., 2002, 12, 3521; DOI: S0960-894X(02)00820-X.

    Article  CAS  Google Scholar 

  8. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, Russ. J. Gen. Chem., 2005, 75, 313; DOI: 1070-3632/05/7502-0313.

    Article  CAS  Google Scholar 

  9. V. D. Romanenko, M. V. Shevchuk, V. P. Kukhar, Curr. Org. Chem., 2011, 15, 2774; DOI: 1385-2728/11.

    Article  CAS  Google Scholar 

  10. Ya. A. Levin, E. I. Vorkunova, Homolytic Chemistry of Phosphorus, Nauka, Moscow, 1978, 318 (in Russian).

    Google Scholar 

  11. A. I. Rakhimov, Synthesis of Organophosphorus Compounds. Homolytic Reactions, Nauka, Moscow, 1985, 22 (in Russian).

    Google Scholar 

  12. Yu. S. Panova, A. V. Sheyanova, E. V. Baranov, A. N. Kornev, Russ. Chem. Bull., 2020, 69, 132; DOI: https://doi.org/10.1007/s11172-020-2734-6.

    Article  CAS  Google Scholar 

  13. Yu. I. Blokhin, I. A. Lubimov, A. M. Bagautdinov, D. K. Gaikov, Russ. Chem. Bull., 2021, 70, 2041; DOI: https://doi.org/10.1007/s11172-021-3315-z.

    Article  CAS  Google Scholar 

  14. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, Heteroatom Chem., 2008, 19, 500; DOI: https://doi.org/10.1002/hc.20469.

    Article  CAS  Google Scholar 

  15. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, Heteroatom Chem., 2017, 28, e21400; DOI: https://doi.org/10.1002/hc.21400.

    Article  Google Scholar 

  16. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, Heteroatom Chem., 2018, 29, e21419; DOI: https://doi.org/10.1002/hc.21419.

    Article  Google Scholar 

  17. D. Nonhebel, J. Tedder, J. Walton, Radicals, Cambridge Univer Press, Cambridge, 1979, 200.

    Google Scholar 

  18. A. A. Prishchenko, M. V. Livantsov, L. I. Livantsova, D. G. Polshchikov, E. V. Grigoriev, Russ. J. Gen. Chem., 1999, 69, 336; DOI: 1070-3632/99/6902.

    CAS  Google Scholar 

  19. E. E. Nifantiev, Chemistry of Hydrophosphoryl Compounds, Nauka, Moscow, 1983, 264 (in Russian).

    Google Scholar 

  20. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, Heteroatom Chem., 2008, 19, 470; DOI: https://doi.org/10.1002/hc.20448.

    Article  CAS  Google Scholar 

  21. A. A. Prishchenko, M. V. Livantsov, V. S. Petrosyan, Russ. J. Gen. Chem., 1994, 64, 1316.

    CAS  Google Scholar 

  22. M. G. Voronkov, V. P. Baryshok, L. P. Petukhov, V. I. Rakhlin, R. G. Mirskov, V. A. Pestunovich, J. Organomet. Chem., 1988, 358, 39; DOI: 0022-328X/88/.

    Article  CAS  Google Scholar 

  23. L. Wozniak, J. Chojnowski, Tetrahedron, 1989, 45, 2465.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. V. Baranin.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 1088–1092, April, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Prishchenko, A.A., Livantsov, M.V., Novikova, O.P. et al. Synthesis of functionalized trimethylsilyl aminomethylphosphinates containing triethoxysilyl moieties. Russ Chem Bull 72, 1088–1092 (2023). https://doi.org/10.1007/s11172-023-3875-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3875-3

Key words

Navigation