Cycloheptyne–cobalt complexes via allylation of stabilized γ-carbonyl cations

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James R. Green


Abstract

The Bu2BOTf mediated reaction of stannylsilanes (5 and 9) with γ-methoxy-alkynoate and -alkynone hexacarbonyldicobalt complexes (8), followed by conversion of the organic carbonyl into an acetate and a BF3·OEt2 mediated intramolecular reaction, affords cycloheptenyne hexacarbonyldicobalt complexes (13 and 15).


References

  1. A. Krebs and J. Wilke, Top. Curr. Chem., 1983, 109, 189 CAS; H. Meier, Adv. Strain Org. Chem., 1991, 1, 215 Search PubMed.
  2. M. J. Went, Adv. Organomet. Chem., 1997, 41, 69 CAS.
  3. The stabilization of other strained alkynes also has been accomplished by complexation to the hexacarbonyldicobalt unit; see Y. Rubin, C. B. Knobler and F. Diederich, J. Am. Chem. Soc., 1990, 112, 4966 Search PubMed; M. H. Haley and B. L. Langsdorf, Chem. Commun., 1997, 1121 CrossRef CAS.
  4. R. S. Dickson and P. J. Fraser, Adv. Organomet. Chem., 1974, 12, 323 CAS.
  5. A. J. M. Caffyn and K. M. Nicholas, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, ed. L. S. Hegedus, Pergamon, Oxford, 1995, vol. 12, ch. 7.1 Search PubMed; K. M. Nicholas, Acc. Chem. Res., 1987, 20, 207 Search PubMed.
  6. N. E. Schore, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, ed. L. S. Hegedus, Pergamon, Oxford, 1995, vol. 12, ch. 7.2 Search PubMed; N. E. Schore, Org. React., 1991, 40, 1 Search PubMed; N. E. Schore, in Comprehensive Organic Synthesis, ed. B. M. Trost, ed. L. A. Paquette, Pergamon, Oxford, 1991, vol. 5, ch. 9.1 CAS; N. E. Schore, Chem. Rev., 1988, 88, 1081 CAS.
  7. S. L. Schreiber, M. T. Klimas and T. Sammakia, J. Am. Chem. Soc., 1986, 108, 3128 CrossRef CAS; T. Nakamura, T. Matsui, K. Tanino and I. Kuwajima, J. Org. Chem., 1997, 62, 3032 CrossRef CAS.
  8. N. E. Schore and S. D. Najdi, J. Org. Chem., 1987, 52, 5296 CrossRef CAS; M. Isobe, C. Yenjai and S. Tanaka, Synlett, 1994, 916 CrossRef CAS; S. Hosokawa and M. Isobe, Synlett, 1995, 1179 CrossRef CAS.
  9. S. Takano, T. Sugihara and K. Ogasawara, Synlett, 1992, 70 CrossRef CAS.
  10. C. S. Vizniowski, J. R. Green, T. L. Breen and A. V. Dalacu, J. Org. Chem., 1995, 60, 7496 CrossRef CAS.
  11. G. E. Keck and D. R. Romer, J. Org. Chem., 1993, 58, 6083 CrossRef CAS.
  12. M. Pereyre, J.-P. Quintard and A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987, pp. 216–218 Search PubMed; A. Yanagisawa, A. Ishiba, H. Nakashima and H. Yamamoto, Synlett, 1997, 88 Search PubMed.
  13. P. A. Jacobi, S. C. Buddhu, D. Fry and S. Rajeswari, J. Org. Chem., 1997, 62, 2894 CrossRef CAS.
  14. Prepared in 90% yield, as adapted from the procedure of J. M. Muchowski, R. Naef and M. L. Maddox, Tetrahedron Lett., 1985, 26, 5375 Search PubMed.
  15. Prepared in 60% yield by the stannylation of 2-chloromethyl-3-trimethylsilylprop-1-ene according to S. Chandrasekhar, S. Latour, J. D. Wuest and B. Zacharie, J. Org. Chem., 1983, 48, 3810 Search PubMed.
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