Polyazacyclophanes containing biphenyl fragments

Abstract

Polyaza[n]cyclophanes containing the 2,2′-biphenyl subunit are prepared in good yields by reaction of the corresponding pertosylated polyamine and 2,2′-bis(bromomethyl)biphenyl in basic media followed by detosylation with Na/Hg; the dynamic behaviour of those receptors is clearly affected by their interaction with different cationic and anionic guests.

References

1. J. Rebek, R. W. Wattley, T. Costello, R. Gadwood and L. Marshall, J. Am. Chem. Soc., 1980, 102, 7398; J. Rebek, Acc. Chem. Res., 1984, 17, 258; F. Gaviña, S. V. Luis, A. M. Costero, M. I. Burguete and J. Rebek, J. Am. Chem. Soc., 1988, 110, 7140; S. V. Luis, M. I. Burguete, F. Gaviña, A. M. Costero and J. Rebek, Bioorg. Med. Chem. Lett., 1991, 1, 87.
2. S. P. Artz and D. J. Cram, J. Am. Chem. Soc., 1984, 106, 2160; R. C. Helgerson, G. R. Weisman, J. L. Toner, T. L. Tarnowski, Y. Chao, J. M. Mayer and D. J. Cram, J. Am. Chem. Soc., 1979, 101, 4928; R. C. Helgerson, T. L. Tarnowski and D. J. Cram, J. Org. Chem., 1979, 44, 2538; V. M. L. J. Aarts, P. D. J. Grootenhuis, D. N. Reinhoudt, A. Czech, B. P. Czech and R. Bartsch, Recl. Trav. Chim. Pays-Bas, 1988, 107, 94; D. N. Reinhoudt, F. de Joy and M. van de Vondervoot, Tetrahedron, 1981, 37, 1985; Tetrahedron, 1981, 37, 1753; H. Kohama, M. Yoshinaga and K. Ishizu, Bull. Chem. Soc. Jpn., 1980, 53, 3707; K. Brandt, I. Powolik, M. Siwy, T. Kupka, R. A. Shaw, D. B. Davies and R. A. Bartsch, J. Am. Chem. Soc., 1996, 118, 4496; J. Am. Chem. Soc., 1997, 119, 12 432.
3. D. P. J. Pearson, S. J. Leigh and I. O. Sutherland, J. Chem. Soc. Perkin Trans. 1, 1979, 3113; A. M. Costero, C. Andreu, R. Martínez-Máñez, J. Soto, L. E. Ochando and J. M. Amigó, Tetrahedron, 1997, 8159.
4. Y. Nagao, T. Miyasaka, K. Seno and E. Fujita, Heterocycles, 1981, 15, 1037.
5. (a) A. Bencini, M. I. Burguete, E. García-España, S. V. Luis, J. F. Miravet and C. Soriano, J. Org. Chem., 1993, 58, 4749; M. I. Burguete, B. Escuder, J. C. Frias, E. García-España, S. V. Luis and J. F. Miravet, J. Org. Chem., 1998, 63, 1810; (b) J. Aguilar, E. García-España, J. A. Guerrero, S. V. Luis, J. M. Llinares, J. F. Miravet, J. A. Ramírez and C. Soriano, J. Chem. Soc., Chem. Commun., 1995, 2237; M. I. Burguete, E. García-España, S. V. Luis, J. F. Miravet, L. Payá, M. Querol and C. Soriano, Chem. Commun., 1998, 1823.