First characterisation of zirconium enolate radical cations in solution and their mesolytic bond cleavage to zirconocene cations

(Note: The full text of this document is currently only available in the PDF Version )

Michael Schmittel and Rolf Söllner


Abstract

Zirconocene enolate radical cations are generated and characterised in solution for the first time; the sterically congested radical cations undergo a mesolytic Zr–O bond cleavage process yielding zirconocene cations, the kinetics of which are determined.


References

  1. I. Paterson, in Comprehensive Organic Synthesis, ed. C. H. Heathcock, Oxford, 1991, vol. 2, p. 301 Search PubMed; D. A. Evans, F. Urpi, T. C. Somers, J. S. Clark and M. T. Bilodeau, J. Am. Chem. Soc., 1990, 112, 8215 Search PubMed; M. P. Bonner and E. R. Thornton, J. Am. Chem. Soc., 1991, 113, 1299 CrossRef CAS; D. A. Evans, D. L. Rieger, M. T. Bilodeau and F. Urpi, J. Am. Chem. Soc., 1991, 113, 1047 CrossRef CAS; R. Mahrwald, Chem. Ber., 1995, 128, 919 CrossRef CAS; R. O. Duthaler and A. Hafner, Chem. Rev., 1992, 92, 807 CAS.
  2. M. Schmittel and R. Söllner, Angew. Chem., Int. Ed. Engl., 1996, 35, 2107 CrossRef CAS; Chem. Ber./Recueil, 1997, 130, 771 Search PubMed.
  3. M. Schmittel, A. Burghart, W. Malisch, J. Reising and R. Söllner, J. Org. Chem., 1998, 63, 396 CrossRef CAS.
  4. Cf. H. H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger and R. Waymouth, Angew. Chem., Int. Ed. Engl., 1995, 34, 1143 Search PubMed and references therein.
  5. J. M. Manriquez, D. R. McAlister, R. D. Sanner and J. E. Bercaw, J. Am. Chem. Soc., 1978, 100, 2716 CrossRef CAS; R. S. Threlkel and J. E. Bercaw, J. Am. Chem. Soc., 1981, 103, 2650 CrossRef CAS; E. J. Moore, D. A. Straus, J. Armantrout, B. D. Santasiero, R. H. Grubbs and J. E. Bercaw, J. Am. Chem. Soc., 1983, 105, 2068 CrossRef CAS; M. D. Curtis, S. Thanedar and W. M. Butler, Organometallics, 1984, 3, 1855 CrossRef CAS; S. Gambarotta, S. Strologo, C. Floriani, A. Chiesi-Villa and C. Guastini, Inorg. Chem., 1985, 24, 654 CrossRef CAS; M. F. Lappert, C. L. Raston, L. M. Engelhardt and A. H. White, J. Chem. Soc., Chem. Commun., 1985, 521 RSC; R. Beckhaus, I. Strauβ and T. Wagner, J. Organomet. Chem., 1994, 464, 155 CrossRef CAS.
  6. M. Schmittel, H. Werner, O. Gevert and R. Söllner, Chem. Ber./Recueil, 1997, 130, 195 CrossRef CAS.
  7. P. G. Gassman, D. W. Macomber and J. W. Hershberger, Organometallics, 1983, 2, 1470 CrossRef CAS; M. J. Burk, W. Tumas, M. D. Ward and D. R. Wheeler, J. Am. Chem. Soc., 1990, 112, 6133 CrossRef CAS.
  8. (a) M. Röck and M. Schmittel, J. Chem. Soc., Chem. Commun., 1993, 1739 RSC; (b) M. Schmittel, G. Gescheidt and M. Röck, Angew. Chem., Int. Ed. Engl., 1994, 33, 1961 CrossRef.
  9. (a) M. Schmittel, J. Heinze and H. Trenkle, J. Org. Chem., 1995, 60, 2726 CrossRef CAS; (b) M. Schmittel, M. Keller and A. Burghart, J. Chem. Soc., Perkin Trans. 2, 1995, 2327 RSC; (c) M. Schmittel, J.-P. Steffen and A. Burghart, Chem. Commun., 1996, 2349 RSC; (d) M. Schmittel and H. Trenkle, Chem. Lett., 1997, 299 CrossRef CAS.
  10. S. L. Borkowsky, R. F. Jordan and G. D. Hinch, Organometallics, 1991, 10, 1268 CrossRef CAS.
  11. R. S. Nicholson and I. Shain, Anal. Chem., 1964, 36, 706 CrossRef CAS.
  12. A. Lasia, J. Electroanal. Chem., Interfacial Electrochem., 1983, 146, 397 CrossRef CAS; J. Heinze, M. Störzbach and M. Mortensen, J. Electroanal. Chem., Interfacial Electrochem., 1984, 165, 61 CrossRef CAS; J. Heinze and M. Störzbach, J. Electroanal. Chem., 1993, 346, 1 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.