Skip to main content
SpringerLink
Log in

Reactions of activated organonickel σ-complexes with elemental (white) phosphorus

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

Abstract

The reactivity of organonickel σ-complexes of the type [NiBr(Ar)(bpy)] (Ar is 2,4,6-tri-methylphenyl (Mes) or 2,4,6-triisopropylphenyl (Tipp); bpy is 2,2′-bipyridine) toward elemental (white) phosphorus was studied. For the reaction to occur, the complexes must be activated by removal of the bromide anion from the coordination sphere of nickel. This can be achieved either in the presence of halogen scavengers or by electrochemical reduction. The arylphosphinic acids ArP(O)(OH)H formed by hydrolysis of organic nickel phosphides are the major reaction products of the overall process.

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.

Similar content being viewed by others

References

  1. Y. Tamaru, Modern Organonickel Chemistry, Wiley-VCH Verlag, Weinheim, 2005, 327 pp.

    Book  Google Scholar 

  2. J. Cámpora, Nickel—Carbon σ-Bonded Complexes, in Comprehensive Organometallic Chemistry III, Elsevier, Amsterdam—Boston, 2007, 8, p. 27.

    Google Scholar 

  3. P. W. Jolly, G. Wilke, The Organic Chemistry of Nickel, Academic Press, London—New York, 1975, Vol. 2, p. 94.

    Book  Google Scholar 

  4. G. P. Chiusoli, P. M. Maitlis, Metal Catalysis in Industrial Organic Processes, RSC Press, Cambridge, 2006, p. 290.

    Book  Google Scholar 

  5. I. P. Beletskaya, L. M. Kustov, Russ. Chem. Rev., 2010, 79, 441.

    Article  CAS  Google Scholar 

  6. Yu. H. Budnikova, Russ. Chem. Rev., 2002, 71, 111.

    Article  CAS  Google Scholar 

  7. J.-Y. Nedelec, J. Perichon, M. Troupel, Organic Electroreductive Coupling Reactions using Transition Metal Complexes as Catalysts, in Topics in Current Chemistry, Ed. E. Steckhan, Springer Verlag, Berlin—Heidelberg, 1997, Vol. 185, p. 141.

    Google Scholar 

  8. T. V. Magdesieva, Elektrokhimiya metalloorganicheskikh soedinenii i metallokompleksov [The Electrochemistry of Organometallic Compounds and Metal Complexes], in Elektrokhimiya organicheskikh soedinenii v nachale XXI veka [The Electrochemistry of Organic Compounds in the Early XXI Century], Eds V. P. Gul’tyai, A. G. Krivenko, A. P. Tomilov, Kompaniya Sputnik+, Moscow, 2008, p. 250 (in Russian).

    Google Scholar 

  9. H. Lund, J. Electrochem. Soc., 2002, 149, No. 4, S21.

    Article  CAS  Google Scholar 

  10. Technology Vision 2020. The U.S. Chemical Industry, ACS Publisher, Washington, 1996, 75 pp.; http://www1.eere.energy.gov/manufacturing/resources/chemicals/pdfs/chem-vision.pdf.

  11. Studies in Inorganic Chemistry, Vol. 20: Phosphorus. An Outline of Its Chemistry, Biochemistry and Uses, 5th ed., Ed. D. E. C. Corbridge, Elsevier, Amsterdam—Lausanne—New York—Oxford—Shannon—Tokyo, 1995, 1208 pp.

    Google Scholar 

  12. V. A. Milyukov, Yu. H. Budnikova, O. G. Sinyashin, Russ. Chem. Rev., 2005, 74, 781.

    Article  CAS  Google Scholar 

  13. M. Peruzzini, L. Gonsalvi, A. Romerosa, Chem. Soc. Rev., 2005, 34, 1038.

    Article  CAS  Google Scholar 

  14. Yu. H. Budnikova, D. G. Yakhvarov, O. G. Sinyashin, J. Organomet. Chem., 2005, 690, 2416.

    Article  CAS  Google Scholar 

  15. D. G. Yakhvarov, E. V. Gorbachuk, R. M. Kagirov, O. G. Sinyashin, Russ. Chem. Bull. (Int. Ed.), 2012, 61, 1300 [Izv. Akad. Nauk, Ser. Khim., 2012, 1285].

    Article  CAS  Google Scholar 

  16. D. G. Yakhvarov, E. A. Trofimova, I. Kh. Rizvanov, O. S. Fomina, O. G. Sinyashin, Elektrokhimiya, 2011, 47, 1180 [Russ. J. Electrochem. (Engl. Transl.), 2011, 47, 1100].

    Google Scholar 

  17. RF Pat. 2396375; Byull. Izobret. [Bulletin of Inventions], 2010, No. 22 (in Russian); http://www.fips.ru.

  18. RF Pat. 85903; Byull. Izobret. [Bulletin of Inventions], 2009, No. 23 (in Russian); http://www.fips.ru.

  19. M. Caporali, L. Gonsalvi, A. Rossin, M. Peruzzini, Chem. Rev., 2010, 110, 4178. Received June 6, 2013; in revised form September 18, 2013

    Article  CAS  Google Scholar 

  20. B. M. Cossairt, N. A. Piro, C. C. Cummins, Chem. Rev., 2010, 110, 4164.

    Article  CAS  Google Scholar 

  21. M. Scheer, G. Balazs, A. Seitz, Chem. Rev., 2010, 110, 4236.

    Article  CAS  Google Scholar 

  22. P. Butti, PhD Thesis, ETH Zürich, 2009, 238 pp.

  23. A. Klein, A. Kaiser, B. Sarkar, M. Wanner, J. Fiedler, Eur. J. Inorg. Chem., 2007, 965.

    Google Scholar 

  24. D. Yakhvarov, E. Trofimova, O. Sinyashin, O. Kataeva, P. Lönnecke, E. Hey-Hawkins, A. Petr, Yu. Krupskaya, V. Kataev, R. Klingeler, B. Büchner, Inorg. Chem., 2011, 50, 4553.

    Article  CAS  Google Scholar 

  25. G. Keglevich, K. Ludanyi, L. D. Quin, Heteroat. Chem., 1997, 8, 135.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    D. G. Yakhvarov, S. V. Kvashennikova & O. G. Sinyashin

  2. Kazan Federal University, 18 ul. Kremlyovskaya, 420008, Kazan, Russian Federation

    D. G. Yakhvarov

Authors
  1. D. G. Yakhvarov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. V. Kvashennikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. G. Sinyashin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to D. G. Yakhvarov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2472–2476, Novemer, 2013.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yakhvarov, D.G., Kvashennikova, S.V. & Sinyashin, O.G. Reactions of activated organonickel σ-complexes with elemental (white) phosphorus. Russ Chem Bull 62, 2472–2476 (2013). https://doi.org/10.1007/s11172-013-0358-9

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-013-0358-9

Key words

Search

Navigation