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Study of the Activity and Stereoselectivity of Some Metathesis Catalysts with Acyclic Internal Olefins

  • F. Lefebvre
  • X. Bories-Azeau
  • J. M. Basset
Part of the NATO Science Series book series (NAII, volume 56)

Abstract

The stereochemistry of the olefin metathesis has been the subject of numerous publications which tried to rationalize the behaviour of various catalysts with acyclic olefins [1-5]. It had been noticed during these studies that a cis olefin gave preferentially a cis olefin and that a trans olefin led essentially to a trans olefin. This was explained in terms of stability of the metallacyclobutanes involved in the catalytic cycle (Scheme 1): the most favoured metallacyclobutanes are those where the substituents in positions 1 and 3 are equatorial. This simple rule allowed the explanation of most experimental results and the configuration retention.

Keywords

Catalytic Cycle Metathesis Reaction Olefin Metathesis Ring Opening Metathesis Grubbs Catalyst 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Leconte, M. and Basset, J.M. (1979) J. Am. Chem. Soc. 101, 7296–7302.CrossRefGoogle Scholar
  2. 2.
    Bilhou, J.L., Basset, J.M., Mutin, R. and Graydon, W.F. (1977) J. Am. Chem. Soc. 99, 4083–4090.CrossRefGoogle Scholar
  3. 3.
    Tinland, B., Quignard, F., Leconte, M. and Basset, J.M. (1983) J. Am. Chem. Soc. 105, 2924–2925.CrossRefGoogle Scholar
  4. 4.
    Basset, J.M., Boutarfa, D., Custodero, E., Leconte, M. and Paillet, C. (1990) The stereochemistry of metathesis of acyclic and cyclic olefins, in Y. Imamoglu (ed.), Olefin Metathesis and Polymerization Catalysts, Kluwer Academic Publishers, Dordrecht, pp. 45–88.Google Scholar
  5. 5.
    Leconte, M. and Basset, J.M. (1979) Nouv. J. Chim. 3, 429–431.Google Scholar
  6. 6.
    Couturier, J.L., Paillet, C., Leconte, M., Basset, J.M. and Weiss, K. (1992) Angew. Chem. Int. Ed. Engl. 31, 628–631.CrossRefGoogle Scholar
  7. 7.
    Lefebvre, F., Leconte, M., Pagano, S., Mutch, A. and Basset, J.M. (1995) Polyhedron 14, 3209–3226.CrossRefGoogle Scholar
  8. 8.
    Ivin, K.J. (1998) J. Mol. Catal. A: Chem. 133, 1–16.CrossRefGoogle Scholar
  9. 9.
    Fürstner, A. (1998) Ruthenium-catalyzed metathesis reactions in organic synthesis, in A. Fürstner (ed.), Alkene Metathesis in Organic Synthesis, Springer, Berlin, pp. 37–72.Google Scholar
  10. 10.
    Nguyen, ST., Johnson, L.K. and Grubbs, R.H. (1992) J. Am. Chem. Soc. 115, 9858–9859.CrossRefGoogle Scholar
  11. 11.
    Ulman, M. and Grubbs, R.H. (1998) Organometallics 17, 2484–2489.CrossRefGoogle Scholar
  12. 12.
    Buchowicz, W. and Mol, J.C. (1999) J. Mol. Catal. A: Chem. 148, 97–103.CrossRefGoogle Scholar
  13. 13.
    Meier, R.J., Aagaard, O.M. and Buda, F. (2000) J. Mol. Catal. A: Chem. 160, 189–197.CrossRefGoogle Scholar
  14. 14.
    Pagano, S. (1995) Métathèse d’oléfines soufrées. Application à l’obtention de thiophènes, Thesis, Lyon, N° 249–95.Google Scholar
  15. 15.
    Lefebvre, F. (2001) Ab initio study of the interaction of ruthenium alkylidene complexes with olefins: Differences between cis and trans olefins, unpublished results.Google Scholar
  16. 16.
    Schrock, R.R. (1990) Acc. Chem. Res. 23, 158–165.CrossRefGoogle Scholar
  17. 17.
    Schrock, R.R., Murdzek, J.S., Bazan, G.C., Robbins, J., DiMare, M. and O’Regan, M. (1990) J. Am. Chem. Soc. 112, 3875–3886.CrossRefGoogle Scholar
  18. 18.
    Schrock, R.R. (1998) Olefin metathesis by well-defined complexes of molybdenum and tungsten, in A. Fürstner (ed.), Alkene Metathesis in Organic Synthesis, Springer, Berlin, pp. 1–36.Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2002

Authors and Affiliations

  • F. Lefebvre
    • 1
  • X. Bories-Azeau
    • 1
  • J. M. Basset
    • 1
  1. 1.Laboratoire de Chimie Organométallique de SurfaceUMR CNRS-CPE 9986Villeurbanne CedexFrance

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