Cycloaddition of nitrile oxides to [60]fullerene

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Tatiana Da Ros, Maurizio Prato, Fabiola Novello, Michele Maggini, Marco De Amici and Carlo De Micheli


Abstract

The addition of nitrile oxides to [60]fullerene is examined and it is found that the reaction products regenerate [60]fullerene under relatively mild conditions; the result is potentially useful for better control of fullerene functionalization.


References

  1. F. Diederich and C. Thilgen, Science, 1996, 271, 317 CrossRef CAS.
  2. A. B. Smith, Tetrahedron, 1996, 52 CrossRef CAS Tetrahedron Symposium in Print on Fullerene Chemistry.
  3. A. Hirsch, I. Lamparth and H. R. Karfunkel, Angew. Chem., Int. Ed. Engl., 1994, 33, 437 CrossRef.
  4. L. Isaacs, R. F. Haldimann and F. Diederich, Angew. Chem., Int. Ed. Engl., 1994, 33, 2339 CrossRef.
  5. I. Lamparth, C. Maichle-Mössmer and A. Hirsch, Angew. Chem., Int. Ed. Engl., 1995, 34, 1607 CrossRef CAS.
  6. F. Cardullo, L. Isaacs, F. Diederich, J.-P. Gisselbrecht, C. Boudon and M. Gross, Chem. Commun., 1996, 797 RSC.
  7. P. R. Birkett, A. G. Avent, A. D. Darwish, H. W. Kroto, R. Taylor and D. R. M. Walton, Chem. Commun., 1996, 1231 RSC.
  8. T. Kusukawa and W. Ando, Angew. Chem., Int. Ed. Engl., 1996, 35, 1315 CrossRef CAS.
  9. B. Kräutler, T. Müller, J. Maynollo, K. Gruber, C. Kratky, P. Ochsenbein, D. Schwartzenbach and H.-B. Bürgi, Angew. Chem., Int. Ed. Engl., 1966, 35, 1204 CrossRef.
  10. M. S. Meier and M. Poplawska, Tetrahedron, 1996, 52, 5043 CrossRef CAS.
  11. H. Irngartinger, C. M. Köhler, U. Huber-Patz and W. Krätschmer, Chem. Ber., 1994, 127, 581 CAS.
  12. K. E. Larsen and K. B. Torssell, Tetrahedron, 1984, 40, 2985 CrossRef CAS.
  13. A. P. Kozikowski, Acc. Chem. Res., 1984, 17, 410 CrossRef CAS.
  14. W. W. Win, M. Kao, M. Eiermann, J. J. McNamara, F. Wudl, D. L. Pole, K. Kassam and J. Warkentin, J. Org. Chem., 1994, 59, 8571.
  15. M. Nitta, A. Yi and T. Kobayashi, Bull. Chem. Soc. Jpn., 1985, 58, 991.
  16. G. Bianchi, R. Gandolfi and P. Grünanger, The Chemistry of Functional Groups, Supplement C, Wiley, New York, N.Y., 1983, p. 748 Search PubMed.
  17. Y.-Z. An, G. A. Ellis, A. L. Viado and Y. Rubin, J. Org. Chem., 1995, 60, 6353 CrossRef CAS.
  18. J. M. Hawkins and A. Meyer, Science, 1993, 260, 1918 CAS.
  19. M. Maggini, G. Scorrano and M. Prato, J. Am. Chem. Soc., 1993, 115, 9798 CrossRef CAS.
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