Regioselective one-step synthesis of trans-3,trans-3,trans-3 and e,e,e [60]fullerene tris-adducts directed by a C₃-symmetrical cyclotriveratrylene tether

Abstract

The first covalent cyclotriveratrylene (CTV)–C₆₀ adducts were prepared by the tether-directed Bingel reaction, which gave the two C₃-symmetrical trans-3,trans-3,trans-3 and e,e,e tris-adducts with a high degree of regioselectivity.

References

1. L. Echegoyen and L. E. Echegoyen, Acc. Chem. Res., 1998, 31, 593.
2. (a) J.-F. Nierengarten, T. Habicher, R. Kessinger, F. Cardullo, F. Diederich, V. Gramlich, J. P. Gisselbrecht, C. Boudon and M. Gross, Helv. Chim. Acta, 1997, 80, 2238; (b) M. Taki, Y. Nakamura, H. Uehara, M. Sato and J. Nishimura, Enantiomer, 1998, 3, 231; (c) H. Isobe, H. Tokuyama, M. Sawamura and E. Nakamura, J. Org. Chem., 1997, 62, 5034.
3. F. Diederich and R. Kessinger, Acc. Chem. Res., in the press..
4. (a) J.-P. Bourgeois, L. Echegoyen, M. Fibbioli, E. Pretsch and F. Diederich, Angew. Chem., Int. Ed. Engl., 1998, 37, 2118; (b) J.-P. Bourgeois, F. Diederich, L. Echegoyen and J.-F. Nierengarten, Helv. Chim. Acta, 1998, 81, 1835.
5. E. Dietel, A. Hirsch, E. Eichhorn, A. Rieker, S. Hackbarth and B. Röder, Chem. Commun., 1998, 1981.
6. (a) A. Hirsch, Top. Curr. Chem., 1999, 199, 1; (b) A. Hirsch, The Chemistry of the Fullerenes, Thieme, Stuttgart, 1994.
7. See for example: (a) A. Hirsch, I. Lamparth and H. R. Karfunkel, Angew. Chem., Int. Ed. Engl., 1994, 33, 437; (b) F. Djojo and A. Hirsch, Chem. Eur. J., 1998, 4, 344; (c) T. Hamano, K. Okuda, T. Mashino, M. Hirobe, K. Arakane, A. Ryu, S. Mashiko and T. Nagano, Chem. Commun., 1997, 21.
8. For tether-directed preparations of tris-adducts, see: L. Isaacs, F. Diederich and R. F. Haldimann, Helv. Chim. Acta, 1997, 80, 317; F. Cardullo, P. Seiler, L. Isaacs, J.-F. Nierengarten, R. F. Haldimann, F. Diederich, T. Mordasini-Denti, W. Thiel, C. Boudon, J.-P. Gisselbrecht and M. Gross, Helv. Chim. Acta, 1997, 80, 343.
9. C. Bingel, Chem. Ber., 1993, 126, 1957.
10. (a) J. W. Steed, P. C. Junk, J. L. Atwood, M. J. Barnes, C. L. Raston and R. S. Burkhalter, J. Am. Chem. Soc., 1994, 116, 10 346; (b) J. L. Atwood, M. J. Barnes, M. G. Gardiner and C. L. Raston, Chem. Commun., 1996, 1449; (c) H. Matsubara, A. Hasegawa, K. shiwaku, K. Asano, M. Uno, S. Takahashi and K. Yamamoto, Chem. Lett., 1998, 923; (d) H. Matsubara, T. Shimura, A. Hasegawa, M. Semba, K. Asano and K. Yamamoto, Chem. Lett., 1998, 1099.
11. J. Canceill, J. Gabard and A. Collet, J. Chem. Soc., Chem. Commun., 1983, 122; J. Canceill, J. Gabard and A. Collet, J. Am. Chem. Soc., 1984, 106, 5997; G. Vériot, J. P. Dutasta, G. Matouzenko and A. Collet, Tetrahedron, 1995, 51, 389.
12. A. Collet, in Comprehensive Supramolecular Chemistry, ed. F. Toda, Pergamon, 1996, vol. 6, ch. 9, pp. 281–303.