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Germylenes and germanium doubly bonded species in heterocyclic organogermanium chemistry. Some results from the Toulouse group. (Review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Germylenes, divalent germanium species, and germanium derivatives with Ge=Y double bonds (Y=C=, O, S, N-, P-) are powerful synthetic reagents in organometallic chemistry. The germylenes exhibit properties analogous to those of carbenes and have been shown to insert into various σ-bonds such as carbon-heteroelement, metal-carbon, and metal-heteroelement of heterocyclic derivatives with ring expansion. The addition of germylenes to various unsaturated compounds (dienes, orthoquinones, carbonyl compounds, imines, nitrosobenzene) leads, as a rule, to cycloadducts with low stability except for dienes and quinones. The doubly bonded germanium species are highly reactive and widely used in organometallic synthesis in various types of reactions such as:

  • - addition (or insertion reactions) to various σ-bonds of organometallic compounds;

  • - insertion reactions with ring expansion of small organic rings;

  • - cycloaddition reactions with 1–2, 1–3, and 1–4 dipolar reagents.

The mechanism and stereochemistry of some reactions are discussed.

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References

  1. J. Satgé, M. Massol, and P. Riviere,J. Organomet. Chem.,56, 1 (1973).

    Google Scholar 

  2. J. Satgé,Bull. Soc. chim. belg.,91, 1019 (1982).

    Google Scholar 

  3. O. M. Nefedov, S. P. Kolesnikov, and A. I. Loffe,Izv. Akad. Nauk SSSR. Ser. Khim., 619 (1976).

  4. P. Riviere, M. Riviere-Baudet, and J. Satgé,Germanium. Comprehensive Organometallic Chem. I,2, chap. 10 (1982).

    Google Scholar 

  5. P. Riviere, M. Riviere-Baudet, and J. Satgé,Germanium. Comprehensive Organometallic Chem. II.,2, chap. 5 (1995).

    Google Scholar 

  6. P. Riviere, A. Castel, J. Satgé, and D. Guyot,J. Organomet. Chem.,315, 157 (1986).

    Google Scholar 

  7. A. I. Neumann,Chem. Rev.,91, 311 (1991).

    Google Scholar 

  8. E. Michels and W. P. Neumann,Tetrahedron Lett.,27, 2455 (1986).

    Google Scholar 

  9. J. Satgé,J. Organomet. Chem.,400, 121 (1990).

    Google Scholar 

  10. P. Riviere and J. Satgé, A. Boy,J. Organomet. Chem.,96, 25 (1975).

    Google Scholar 

  11. J. Satgé,Pure Appl. Chem.,56, 137 (1984).

    Google Scholar 

  12. C. Couret, J. Escudié, P. Riviere, S. Satgé, and G. Redoules,J. Organomet. Chem.,84, 191 (1975).

    Google Scholar 

  13. J. Satgé,Frontiers of organogermanium,-tin and-lead chemistry, Eds. E. Lukevics, L. Ignatovich. Riga, (1993), p. 55.

  14. H. Lavayssiere, G. Dousse, and J. Satgé,Phosphorus, Sulfur, Silicon.,53, 411 (1990).

    Google Scholar 

  15. Ph. Meunier, B. Gautheron, G. Dousse, H. Lavayssiere, and J. Satgé, unpublished results.

  16. C. Couret, J. Satgé, J. Escudié, and J. D. Andriamizaka,J. Organomet. Chem.,132, C5 (1977).

    Google Scholar 

  17. A. Castel, P. Riviere, J. Satgé, and M. Ahbala,J. Organomet. Chem.,331, 11 (1987).

    Google Scholar 

  18. J. Satgé,Adv. Organomet. Chem.,21, 241 (1982).

    Google Scholar 

  19. J. Satgé,Rev. Silicon, germanium,-tin and-lead Cpds.,8, 291 (1985).

    Google Scholar 

  20. J. Barrau, J. Escudié, and J. Satgé,Chem. Rev.,90, 283 (1990).

    Google Scholar 

  21. J. Escudié, C. Couret, H. Ranaivonjatovo, and J. Satgé,Coord. Chem. Rev.,130, 427 (1994).

    Google Scholar 

  22. J. Escudié, C. Couret, H. Ranaivonjatovo, G. Anseime, G. Delpon-Lacaze, M. A. Chaubon, A. Kandri-Rodi, and J. Satgé,Main Group Metal Chem.,17, 33 (1994).

    Google Scholar 

  23. M. Riviere-Baudet,Main Group Metal Chem.,18, 353 (1995).

    Google Scholar 

  24. M. A. Chaubon, H. Ranaivonjatovo, J. Escudié, and J. Satgé,Main Group Metal Chem.,19, 145 (1996).

    Google Scholar 

  25. A. Kandri-Rodi, H. Ranaivonjatovo, J. Escudié, and A. Kerbal,Main Group Metal Chem.,19, 199 (1996).

    Google Scholar 

  26. J. Escudié, C. Couret, and H. Ranaivonjatovo,Coord. Chem. Rev.,178/180, 565 (1998).

    Google Scholar 

  27. J. Barrau and G. Rima,Coord. Chem. Rev.,178/180, 593 (1998).

    Google Scholar 

  28. P. Riviere, A. Castel, and J. Satgé,J. Am. Chem. Soc.,102, 5413 (1980).

    Google Scholar 

  29. M. Lazraq,Thesis Toulouse (1988).

  30. M. Lazraq, C. Couret, J. Escudié, and J. Satgé,Organometallics,10, 1971 (1991).

    Google Scholar 

  31. C. Couret, J. Escudié, J. Satgé, and M. Lazraq,J. Am. Chem. Soc.,109, 4411 (1987).

    Google Scholar 

  32. M. Lazraq, C. Couret, J. P. Declercq, A. Dubourg, J. Escudié, and M. Riviere-Baudet,Organometallics,9, 845 (1990).

    Google Scholar 

  33. M. Lazraq, J. Escudié, C. Couret, J. Satgé, and M. Soufiaoui,J. Organomet. Chem.,397, 1 (1990).

    Google Scholar 

  34. M. P. Egorov, S. P. Kolesnikov, O. M. Nefedov, and A. Krebs,J. Organomet. Chem.,375, C5 (1989).

    Google Scholar 

  35. M. Lazraq, J. Escudié, C. Couret, U. Bergsträsser, and M. Regitz,J. Chem. Soc. Chem. Commun., 569 (1993).

  36. G. Lacrampe, H. Lavayssiere, M. Riviere-Baudet, and J. Satgé,Rec. Trav. Chem. Pays-Bas.,102, 21 (1983).

    Google Scholar 

  37. M. Riviere-Baudet, P. Riviere, A. Castel, G. Lacrampe, and J. Satgé,Rec. Trav. Chem. Pays-Bas.,102, 65 (1983).

    Google Scholar 

  38. N. Wiberg, G. Preiner, P. Karampatses, and C. H. Khim, K. Schurz,Chem. Ber.,120, 1357 (1987).

    Google Scholar 

  39. K. Khallaayoun,Thesis Ph. D. Agadir, Marocco, 1993.

  40. J. Escudié, C. Couret, J. Satgé, and J. D. Andriamizaka,Organometallics,1, 1261 (1982).

    Google Scholar 

  41. C. Couret, J. Satgé, J. D. Andriamizaka, and J. Escudié,J. Organomet. Chem.,157, C35 (1978).

    Google Scholar 

  42. M. Andrianarison, C. Couret, J. P. Declercq, A. Dubourg, J. Escudié, H. Ranaivonjatovo, and J. Satgé,Organometallics,7, 1545 (1988).

    Google Scholar 

  43. H. Ranaivonjatovo, J. Escudié, C. Couret, and J. Satgé,J. Organomet. Chem.,415, 327 (1991).

    Google Scholar 

  44. H. Ranaivonjatovo, J. Escudié, C. Couret, J. P. Declercq, A. Dubourg, and J. Satgé,Organometallics,12, 1674 (1993).

    Google Scholar 

  45. J. M. Andrianarison, C. Couret, J. P. Declercq, A. Dubourg, J. Escudié, and J. Satgé,J. Chem. Soc. Chem. Commun., 921 (1987).

  46. G. Trinquier, M. Pelissier, Roch B. Saint, and H. Lavayssiere,J. Organomet. Chem.,214, 169 (1981).

    Google Scholar 

  47. J. Barrau, G. Rima, H. Lavayssiere, G. Dousse, and J. Satgé,J. Organomet. Chem.,246, 227 (1983).

    Google Scholar 

  48. H. Lavayssiere, G. Dousse, J. Satgé, J. Barrau, and M. Traoré,Angew. Chem. Intern. Ed. Engl.,21, 447 (1982).

    Google Scholar 

  49. H. Lavayssiere, J. Satgé, J. Barrau, and M. Traoré,J. Organomet. Chem.,240, 335 (1982).

    Google Scholar 

  50. J. Bodiguel, Ph. Meunier, M. M. Kubicki, Ph. Richard, B. Gautheron, G. Dousse, H. Lavayssiere, and J. Satgé,Organometallics,11, 1423 (1992).

    Google Scholar 

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Authors
  1. Jacques Satgé
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Additional information

In commemoriation of 100 years of Academician A. N. Nesmeyanov birth.

Université Paul Sabatier Toulouse, France. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1155–1175, September, 1999.

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Satgé, J. Germylenes and germanium doubly bonded species in heterocyclic organogermanium chemistry. Some results from the Toulouse group. (Review). Chem Heterocycl Compd 35, 1013–1032 (1999). https://doi.org/10.1007/BF02251793

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  • DOI: https://doi.org/10.1007/BF02251793

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