Resolution and circular dichroism of an asymmetrically cage-opened [60]fullerene derivative

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

Jan C. Hummelen , Majid Keshavarz-K , Joost L. J. van Dongen , René A. J. Janssen , E. W. Meijer and Fred Wudl


Abstract

The enantiomers of the first cagewise inherently asymmetric C 60 derivative, i.e. N-MEM (MEM = 2-methoxyethoxymethyl) keto lactam 1, have been separated by HPLC and their chiroptical properties compared with data obtained from C 60 derivatives that are dissymmetric or asymmetric due to chiral addends.


References

  1. J. C. Hummelen, M. Prato and F. Wudl, J. Am. Chem. Soc., 1995, 117, 7003 CrossRef CAS.
  2. J. C. Hummelen, B. Knight, J. Pavlovich, R. González and F. Wudl, Science, 1995, 269, 1554 CrossRef CAS.
  3. M. Keshavarz-K, R. González, R. G. Hicks, G. Srdanov, V. I. Srdanov, T. G. Collins, J. C. Hummelen, C. Bellavia-Lund, J. Pavlovich, F. Wudl and K. Holczer, Nature, 1996, 383, 147 CrossRef.
  4. K. Prassides, M. Keshavarz-K, J. C. Hummelen, W. Andreoni, P. Giannozzi, E. Beer, C. Bellavia, L. Cristofolini, R. González, A. Lappas, Y. Murata, M. Malecky, V. I. Srdanov and F. Wudl, Science, 1996, 271, 1833 CrossRef CAS.
  5. F. Diederich, C. Thilgen and A. Herrmann, Nachr. Chem. Tech. Lab., 1996, 44, 9 Search PubMed.
  6. C. Thilgen, A. Herrmann and F. Diederich, Helv. Chim. Acta, 1997, 80, 183 CrossRef CAS.
  7. A. Vasella, P. Uhlmann, C. A. A. Waldraff, F. Diederich and C. Thilgen, Angew. Chem., 1992, 104, 1388.
  8. A. Bianco, M. Maggini, G. Scorrano, C. Toniolo, G. Marconi, C. Villani and M. Prato, J. Am. Chem. Soc., 1996, 118, 4072 CrossRef CAS.
  9. M. Maggini, G. Scorrano, A. Bianco, C. Toniolo and M. Prato, Tetrahedron Lett., 1995, 36, 2845 CrossRef CAS.
  10. J. M. Hawkins, A. Meyer and M. Nambu, J. Am. Chem. Soc., 1993, 115, 9844 CrossRef CAS.
  11. A. Hirsch, I. Lamparth and H. R. Karfunkel, Angew. Chem., 1994, 106, 453 CAS.
  12. F. Diederich and R. L. Whetten, Acc. Chem. Res., 1992, 25, 119 CrossRef CAS; S. Iijima, Nature, 1991, 354, 56 CrossRef CAS.
  13. J. M. Hawkins and A. Meyer, Science, 1993, 260, 1918 CAS; J. M. Hawkins, M. Nambu and A. Meyer, J. Am. Chem. Soc., 1994, 116, 7642 CrossRef CAS.
  14. M. S. Newman, R. S. Darlak and L. Tsai, J. Am. Chem. Soc., 1967, 89, 6191 CrossRef CAS.
  15. S. R. Wilson, Q. Lu, J. Cao, Y. Wu, C. J. Welch and D. I. Schuster, Tetrahedron, 1996, 52, 5131 CrossRef CAS.
  16. M. Maggini, G. Scorrano, A. Bianco, C. Toniolo, R. P. Sijbesma, F. Wudl and M. Prato, J. Chem. Soc., Chem. Commun., 1994, 305 RSC.
  17. F. Novello, M. Prato, T. Da Ros, M. De Amici, A. Bianco, C. Toniolo and M. Maggini, Chem. Commun., 1996, 903 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.