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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 12, pp 1584–1589 | Cite as

Germylenes derived from pyridine-containing diols: reactions with diphenylphosphoryl azide and 9,10-phenanthrenequinone*

  • M. Huang
  • M. M. Kireenko
  • K. V. Zaitsev
  • Yu. F. Oprunenko
  • A. V. Churakov
  • S. S. KarlovEmail author
  • G. S. Zaitseva
Article

A study was carried out on the behavior of monomeric germylenes derived from pyridine-containing diols in reactions with diphenylphosphoryl azide and 9,10-phenanthrenequinone. It was found that the germanium atom increases its oxidation state to 4+ in these reactions. The structure of the product of the reaction with 9,10-phenanthrenequinone was confirmed by X-ray structural analysis, which showed a transannular germanium-nitrogen interaction in this product.

Keywords

germylenes hypervalent germanium pyridine-containing diols 1,4-cycloaddition oxidation X-ray structural analysis 

Reference

  1. 1.
    Y. Mizuhata, T. Sasamori, and N. Tokitoh, Chem. Rev., 109, 3479 (2009).CrossRefGoogle Scholar
  2. 2.
    N. Tokitoh and R. Okazaki, Coord. Chem. Rev., 210, 251 (2000).CrossRefGoogle Scholar
  3. 3.
    W. P. Neumann, Chem. Rev., 91, 311 (1991).CrossRefGoogle Scholar
  4. 4.
    D. H. Harris and M. F. Lappert, J. Chem. Soc., Chem. Commun., 895 (1974).Google Scholar
  5. 5.
    P. J. Davidson, D. H. Harris, and M. F. Lappert, J. Chem. Soc., Dalton Trans., 2268 (1976).Google Scholar
  6. 6.
    A. Herve, A. L. Rodriguez, and E. Fouquet, J. Org. Chem., 70, 1953 (2005).CrossRefGoogle Scholar
  7. 7.
    O. Dechy-Cabaret, B. Martin-Vaca, and D. Bourissou, Chem. Rev., 104, 6174 (2004).CrossRefGoogle Scholar
  8. 8.
    H. Gerung, S. D. Bunge, T. J. Boyle, C. J. Brinker, and S. M. Han, Chem. Commun., 1914 (2005).Google Scholar
  9. 9.
    M. Huang, E. Kh. Lermontova, K. V. Zaitsev, A. V. Churakov, Yu. F. Oprunenko, J. A. K. Howard, S. S. Karlov, and G. S. Zaitseva, J. Organomet. Chem., 694, 3828 (2009).CrossRefGoogle Scholar
  10. 10.
    J. Barrau, G. Rima, and T. El Amraoui, J. Organomet. Chem., 570, 163 (1998).CrossRefGoogle Scholar
  11. 11.
    A. Meller, G. Ossig, W. Maringgele, M. Noltemeyer, D. Stalke, R. Herbst-Irmer, S. Freitag, and G. M. Sheldrick, Z. Naturforsch., B: Chem. Sci., 47, 162 (1992).Google Scholar
  12. 12.
    M. Huang, Chemical Sciences Candidate's Dissertation, Moscow (2010).Google Scholar
  13. 13.
    M. Huang, M. M. Kireenko, E. Kh. Lermontova, A. V. Churakov, Yu. F. Oprunenko, K. V. Zaitsev, S. S. Karlov, D. A. Lemenovskii, and G. S. Zaitseva, Butlerov Commun., 24, 26 (2011).Google Scholar
  14. 14.
    D. Matioszek, N. Katir, N. Saffon, and A. Castel, Organometallics, 29, 3039 (2010).CrossRefGoogle Scholar
  15. 15.
    D.-H. Chen and H.-C. Chiang, J. Chin. Chem. Soc., 40, 373 (1993).Google Scholar
  16. 16.
    H.-C. Chiang, S.-M. Lin, and C.-H. Ueng, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 48, 991 (1992).CrossRefGoogle Scholar
  17. 17.
    S. N. Gurkova, A. I. Gusev, N. V. Alekseev, T. K. Gar, and N. A. Viktorov, Zh. Strukt. Khim., 31, 158 (1990).Google Scholar
  18. 18.
    S. S. Karlov, E. K. Yakubova, E. V. Gauchenova, A. A. Selina, A. V. Churakov, J. A. K. Howard, D. A. Tyurin, J. Loberth, and G. S. Zaitseva, Z. Naturforsch., B: Chem. Sci., 58, 1165 (2003).Google Scholar
  19. 19.
    E. Kh. Lermontova, A. A. Selina, S. S. Karlov, A. V. Churakov, J. A. K. Howard, Yu. F. Oprunenko, M. Yu. Antipin, J. Sundermeyer, and G. S. Zaitseva, J. Organomet. Chem., 691, 5710 (2006).CrossRefGoogle Scholar
  20. 20.
    G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • M. Huang
    • 1
  • M. M. Kireenko
    • 1
  • K. V. Zaitsev
    • 1
  • Yu. F. Oprunenko
    • 1
  • A. V. Churakov
    • 2
  • S. S. Karlov
    • 1
    Email author
  • G. S. Zaitseva
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityMoscowRussia
  2. 2.N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of SciencesMoscowRussia

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