Molecular Design of a "Molecular Syringe" Mimic for Metal Cations Using a 1,3-Alternate Calix[4]arene Cavity

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3568-3574

  Ikeda, Atsushi ^a   Tsudera, Takanobu ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000129390     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962040k     Document Type: Article

References (66)

1. Raymond, K. N.; Carrano, C. J. Acc. Chem. Res. 1979, 12, 183.
2. Choy, E. M.; Evans, D. F.; Cussler, E. L. J. Am. Chem. Soc. 1974, 96, 7058.
3. Cram, D. J. Science 1983, 219, 1177 and references cited therein.
4. Lehn, J.-M. Science 1985, 227, 849 and references cited therein.
5. Gokel, G. W. In Crown Ethers & Cryptands; Royal Society of Chemistry: Cambridge, 1991.
6. (a) Arduini, A.; Pochini, A.; Reverberi, S.; Ungaro, R. Tetrahedron 1986, 42, 2089.
7. (b) Andreetti, G. D.; Calestani, G.; Ugozzoli, F.; Auduini, A.; Ghidini, E.; Pochini, A.; Ungaro, R. J. Incl. Phenom. 1987, 5, 123.
8. Chang, S.-K.; Cho, I. J. Chem. Soc., Perkin Trans. 1 1986, 211.
9. McKervey, M. A.; Seward, E. M.; Ferguson, G.; Ruhl, B.; Harris, S. J. Chem. Soc., Chem. Commun. 1985, 388.
10. Arnaud-Neu, F.; Collins, E. M.; Deasy, M.; Ferguson, G.; Harris, S. J.; Kaitner, B.; Lough, A. J.; McKervey, M. A.; Marques, E.; Ruhl, B. L.; Schwing Weill, M. J.; Seward, E. M. J. Am. Chem. Soc. 1989, 111, 8681.
11. Arimura, T.; Kubota, M.; Matsuda, T.; Manabe, O.; Shinkai, S. Bull. Chem. Soc. Jpn. 1989, 62, 1674.
12. (a) Shinkai, S.; Otsuka, T.; Fujimoto, K.; Matsuda, T. Chem. Lett. 1990, 835.
13. (b) Yamamoto, H.; Shinkai, S. Ibid. 1994, 1115.
14. (c) Yamamoto, H.; Ueda, K.; Sandanayake, K. R. A. S.; Shinkai, S. Ibid. 1995, 497.
15. (d) Yamamoto, H.; Ueda, K.; Suenaga, H.; Sakaki, T.; Shinkai, S. Ibid. 1996, 39.
16. For comprehensive reviews see (a) Gutsche, C. D. In Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
17. (b) Vicens, J.; Böhmer, V., Eds. In Calixarenes; Kluwer Academic Press: Dordrecht, 1991.
18. (c) Shinkai, S. Bioorg. Chem. Front. 1990, 1, 161.
19. (d) Idem. Tetrahedron 1993, 49, 8933.
20. (e) Böhmer, V. Angew. Chem., Ind. Ed. Engl. 1995, 34, 713.
21. (a) Iwamoto, K.; Araki, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4955.
22. (b) Iwamoto, K.; Araki, K.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1 1991, 1161.
23. (c) Iwamoto, K.; Araki, K.; Shinkai, S. Tetrahedron 1991, 47, 4325.
24. Shinkai, S.; Fujimoto, K; Otsuka, T.; Herman, H. L. J. Org. Chem. 1992, 75, 1516.
25. Iwamoto, K.; Shinkai, S. J. Org. Chem. 1992, 57, 7066.
26. Gutsche, C. D.; Reddy, P. A. J. Org. Chem. 1991, 56, 4783.
27. See, K. A.; Fronczek, F. R.; Watson, W. H.; Kashyap, R. P.; Gutsche, C. D. J. Org. Chem. 1991, 56, 7256.
28. Iqbal, M.; Mangiafico, T.; Gutsche, C. D. Tetrahedron 1987, 43, 4917.
29. Verboom, W.; Datta, S.; Asfari, Z.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1992, 57, 5394.
30. (a) Dijkstra, P. J.; Brunink, J. A. J.; Bugge, K.-E.; Reinhoudt, D. N.; Harkema, S.; Ungaro, R.; Ugozzoli, F.; Ghidini, E. J. Am. Chem. Soc. 1989, 111, 7567.
31. (b) Ghidini, E.; Ugozzoli, F.; Ungaro, R.; Harkema, S.; El-Fadl, A. A.; Reinhoudt, D. N. Ibid. 1990, 112, 6979.
32. (c) van Loon, J.-D.; Groenen, L. C.; Wijmenga, S. S.; Verboom, W.; Reinhoudt, D. N. Ibid. 1991, 113, 2378.
33. (a) Alfieri, C.; Dradi, E.; Pochini, A.; Ungaro, R.; Andreetti, G. D. J. Chem. Soc., Chem. Commun. 1983, 1075.
34. (b) Arduini, A.; Casnati, A.; Dodi, L.; Pochini, A.; Ungaro, R. Ibid. 1990, 1597.
35. (c) Arduini, A.; Casnati, A.; Fabbi, M.; Minari, P.; Pochini, A.; Sicuri, A. R.; Ungaro, R. Supramol. Chem. 1993, 1, 235.
36. Gutsche, C. D.; See, K. A. J. Org. Chem. 1992, 57, 4527.
37. (a) Böhmer, V.; Goldmann, H.; Vogt, W. J. Chem. Soc., Chem. Commun. 1985, 667.
38. (b) Goldmann, H.; Vogt, W.; Paulus, E.; Böhmer, V. J. Am. Chem. Soc. 1988, 110, 6811,
39. (c) Böhmer, V.; Vogt, W.; Goldmann, H. J. Org. Chem. 1990, 55, 2569.
40. (a) Araki, K.; Akao, K.; Otsuka, H.; Nakashima, K.; Inokuchi, F.; Shinkai, S. Chem. Lett. 1994, 1251.
41. (b) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032.
42. (c) Otsuka, H.; Araki, K.; Matsumoto, H.; Harada, T.; Shinkai, S. J. Org. Chem. 1994, 59, 4032,
43. (d) Otsuka, H.; Shinkai, S. J. Am. Chem. Soc. 1996, 118, 4271.
44. (a) Ikeda, A.; Shinkai, S. J. Am. Chem. Soc. 1994, 116, 3102.
45. (b) Koh, N. K.; Araki, K.; Shinkai, S.; Asfari, Z.; Vicens, J. Tetrahedron Lett. 1995, 36, 6095.
46. For the π-donor participation (to the metal-binding) see (a) Iyoda, M.; Kuwatani, Y.; Yamauchi, T.; Oda, J. J. Chem. Soc., Chem. Commun. 1988, 65. (b) Leookes, R.; Vögtle, F. Chem. Ber. 1983, 116, 215. (c) Pierre, J.-L.; Baret, P.; Chautemps, P.; Armand, M. J. Am. Chem. Soc. 1981, 103, 2986. (d) Kang, H. C.; Hanson, A. W.; Eaton, B.; Boekelheide, V. Ibid. 1985, 107, 1979. (e) Heirtzler, F. R.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Lehne, V. J. Org. Chem. 1993, 58, 2781. (f) Gano, J. E.; Subramaniam, G.; Birnbaum, R. Ibid. 1990, 55, 4760.
47. For the π-donor participation (to the metal-binding) see (a) Iyoda, M.; Kuwatani, Y.; Yamauchi, T.; Oda, J. J. Chem. Soc., Chem. Commun. 1988, 65. (b) Leookes, R.; Vögtle, F. Chem. Ber. 1983, 116, 215. (c) Pierre, J.-L.; Baret, P.; Chautemps, P.; Armand, M. J. Am. Chem. Soc. 1981, 103, 2986. (d) Kang, H. C.; Hanson, A. W.; Eaton, B.; Boekelheide, V. Ibid. 1985, 107, 1979. (e) Heirtzler, F. R.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Lehne, V. J. Org. Chem. 1993, 58, 2781. (f) Gano, J. E.; Subramaniam, G.; Birnbaum, R. Ibid. 1990, 55, 4760.
48. For the π-donor participation (to the metal-binding) see (a) Iyoda, M.; Kuwatani, Y.; Yamauchi, T.; Oda, J. J. Chem. Soc., Chem. Commun. 1988, 65. (b) Leookes, R.; Vögtle, F. Chem. Ber. 1983, 116, 215. (c) Pierre, J.-L.; Baret, P.; Chautemps, P.; Armand, M. J. Am. Chem. Soc. 1981, 103, 2986. (d) Kang, H. C.; Hanson, A. W.; Eaton, B.; Boekelheide, V. Ibid. 1985, 107, 1979. (e) Heirtzler, F. R.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Lehne, V. J. Org. Chem. 1993, 58, 2781. (f) Gano, J. E.; Subramaniam, G.; Birnbaum, R. Ibid. 1990, 55, 4760.
49. For the π-donor participation (to the metal-binding) see (a) Iyoda, M.; Kuwatani, Y.; Yamauchi, T.; Oda, J. J. Chem. Soc., Chem. Commun. 1988, 65. (b) Leookes, R.; Vögtle, F. Chem. Ber. 1983, 116, 215. (c) Pierre, J.-L.; Baret, P.; Chautemps, P.; Armand, M. J. Am. Chem. Soc. 1981, 103, 2986. (d) Kang, H. C.; Hanson, A. W.; Eaton, B.; Boekelheide, V. Ibid. 1985, 107, 1979. (e) Heirtzler, F. R.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Lehne, V. J. Org. Chem. 1993, 58, 2781. (f) Gano, J. E.; Subramaniam, G.; Birnbaum, R. Ibid. 1990, 55, 4760.
50. For the π-donor participation (to the metal-binding) see (a) Iyoda, M.; Kuwatani, Y.; Yamauchi, T.; Oda, J. J. Chem. Soc., Chem. Commun. 1988, 65. (b) Leookes, R.; Vögtle, F. Chem. Ber. 1983, 116, 215. (c) Pierre, J.-L.; Baret, P.; Chautemps, P.; Armand, M. J. Am. Chem. Soc. 1981, 103, 2986. (d) Kang, H. C.; Hanson, A. W.; Eaton, B.; Boekelheide, V. Ibid. 1985, 107, 1979. (e) Heirtzler, F. R.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Lehne, V. J. Org. Chem. 1993, 58, 2781. (f) Gano, J. E.; Subramaniam, G.; Birnbaum, R. Ibid. 1990, 55, 4760.
51. For the π-donor participation (to the metal-binding) see (a) Iyoda, M.; Kuwatani, Y.; Yamauchi, T.; Oda, J. J. Chem. Soc., Chem. Commun. 1988, 65. (b) Leookes, R.; Vögtle, F. Chem. Ber. 1983, 116, 215. (c) Pierre, J.-L.; Baret, P.; Chautemps, P.; Armand, M. J. Am. Chem. Soc. 1981, 103, 2986. (d) Kang, H. C.; Hanson, A. W.; Eaton, B.; Boekelheide, V. Ibid. 1985, 107, 1979. (e) Heirtzler, F. R.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Lehne, V. J. Org. Chem. 1993, 58, 2781. (f) Gano, J. E.; Subramaniam, G.; Birnbaum, R. Ibid. 1990, 55, 4760.
52. (a) Dougherty, D. A.; Stauffer, D. A. Science 1990, 250, 1558.
53. (b) Dougherty, D. A. Ibid. 1996, 271, 163 and references cited therein.
54. Kim, K. S.; Lee, J. Y.; Lee, S. J.; Ha, T.-K.; Kim, D. H. J. Am. Chem. Soc. 1994, 116, 7399.
55. Inokuchi, F.; Miyahara, Y.; Inazu, T.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1364.
56. The similar idea with a switch function has been applied to a molecular shuttle: Bissell, R. A.; Cordova, E.; Kaifer, A. E.; Stoddart, J. F. Nature 1994, 369, 133.
57. Ungaro, R.; Casnati, A.; Ugozzoli, F.; Pochini, A.; Dozol, J.-F.; Hill, C.; Rouquette, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1506.
58. Casnati, A.; Pochini, A.; Ungaro, R.; Ugozzoli, F.; Arnaud, F.; Fanni, S.; Schwing, M.-J.; Egberink, R. J. M.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 2767.
59. + ionophores see (a) Iwema, W. I.; Verboom, W.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1994, 71. (b) Perez-Adelmar, J. -A.; Abraham, H.; Sanchez, C.; Rissanen, K.; Prados, P.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1009.
60. + ionophores see (a) Iwema, W. I.; Verboom, W.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1994, 71. (b) Perez-Adelmar, J. -A.; Abraham, H.; Sanchez, C.; Rissanen, K.; Prados, P.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1009.
61. 1H NMR spectral data indicate, however, that this path occurs incomparably more slowly than the intramolecular metal-tunneling path. One can consider, therefore, that upon protonation of the ring nitrogen the metal cation moves to the another side predominantly via the calix[4]arene tube.
62. Takeda, Y.; Yano, H. Bull. Chem. Soc. Jpn. 1980, 53, 1720.
63. Shinkai, S.; Inuzuka, K.; Miyazaki, O.; Manabe, O. J. Am. Chem. Soc. 1985, 107, 3950.
64. Shinkai, S.; Araki, K.; Manabe, O. J. Am. Chem. Soc. 1988, 110, 7214.
65. (a) Deng, G.; Sakaki, T.; Nakashima, K.; Shinkai, S. Chem. Lett. 1992, 1287.
66. (b) Deng, G.; Sakaki, T.; Shinkai, S. J. Polym. Sci., Polym. Chem. 1993, 31, 1915.