Alkali metal cation selectivity of an oligo-ether substituted norbornadiene and quadricyclane isomer

European Journal of Organic Chemistry

Volumn , Issue 23, 2001, Pages 4419-4422

  Herges, Rainer ^a   Winkler, Torsten ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

Alkali metals; Association constants; Isomerization; Molecular modeling; Octopus ligand

Indexed keywords

ALKALI METAL; CATION; CESIUM; CHLOROFORM; ETHER DERIVATIVE; LITHIUM; NORBORNADIENE DERIVATIVE; POLYETHER DERIVATIVE; POTASSIUM; QUADRICYCLANE DERIVATIVE; SODIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; EXTRACTION; ISOMERISM; MOLECULAR MODEL;

EID: 0035214111     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200112)2001:23<4419::aid-ejoc4419>3.0.co;2-c     Document Type: Article

References (45)

1. [1a] A. Royant, K. Edman, T. Ursby, E. Pebay-Peyroula, E. M. Landau, R. Neutze, Nature 2000, 406, 645-648;
2. [1b] H. J. Sass, G. Büldt, R. Gessenich, D. Hehn, D. Neff, R. Schlesinger, J. Berendzen, P. Ormos, Nature 2000, 406, 649-653;
3. [1c] S. Subramanian, R. Henderson, Nature 2000, 406, 653-657;
4. I. Spasojevic, A. L. Crumbliss, Inorg. Chem. 1999, 38, 3248-3250;
5. [1d] Y. Nakatsuji, M. Muraoka, M. Wada, H. Morita, A. Masuyama, T. Kida, I. Ikeda, J. Org. Chem. 1997, 62, 6231-6235;
6. [1e] G. Steinberg-Yfrach, P. A. Lidell, S. C. Hung, A. L. Moore, D. Gust, T. A. Moore, Nature 1997, 385, 239-241;
7. [1f] M. F. Paugam, L. S. Valencia, B. Boggess, B. D. Smith, J. Am. Chem. Soc. 1994, 116, 11203-11204;
8. [1g] G. T. Morin, M. F. Paugam, M. P. Hughes, B. D. Smith, J. Org. Chem. 1994, 59, 2724-2728;
9. [1h] M. F. Paugam, G. T. Morin, B. D. Smith, Tetrahedron Lett. 1993, 34, 7841-7844;
10. [1i] M. F. Paugam, B. D. Smith, Tetrahedron Lett. 1993, 34, 3723-3726;
11. [1j] S. Yoshida, T. Watanabe, Bull. Chem. Soc. Jpn. 1990, 63, 3508-3515;
12. [1k] H. Sasaki, A. Ueno, T. Osa, Bull. Chem. Soc. Jpn. 1988, 61, 2321-2325;
13. [1l] S. Shinkai, M. Ishihara, K. Ueda, O. Manabe, J. Chem. Soc., Chem. Commun. 1984, 724;
14. [1m] H. Tsukube, J. Membr. Sci. 1983, 14, 155-160;
15. [1n] S. Shinkai, H. Kinda, Y. Araragi, O. Manabe, Bull. Chem. Soc. Jpn. 1983, 56, 559;
16. [1o] M. Raban, J. Greenblatt, F. Kandil, J. Chem. Soc., Chem. Commun. 1983, 1409;
17. [1p] S. Shinkai, T. Minami, Y. Kusano, O. Manabe, J. Am. Chem. Soc. 1982, 104, 1967;
18. [1q] K. Maruyama, H. Tsukube, T. Araki, Tetrahedron Lett. 1981, 22, 2001-2004;
19. [1r] I. Tabushi, Y. Kobuke, J. Imuta, J. Am. Chem. Soc. 1980, 102, 1744-1745.
20. [2a] R. Herges, W. Reif, Chem. Ber. 1994, 127, 1143-1145;
21. [2b] R. Herges, W. Reif, Liebigs Ann. 1996, 761-768;
22. [2c] F. Starck, P. G. Jones, R. Herges, Eur. J. Org. Chem. 1998, 2533-2539;
23. [2d] R. Herges, F. Starck, T. Winkler, M. Schmittel, Chem. Eur. J. 1999, 5, 2965-2969.
24. For review see: [3a] K. Hirao, A. Yamashida, O. Yonemitsu, Studies on Valence Isomerization Between Norbornadiene and Quandricyclane (Eds.: E. Osawa, O. Yonemitsu), VCH Publishers 1992;
25. see also: [3b] K. Maruyama, H. Tamiaki, S. Kawabata, Chem. Lett. 1984, 743-746;
26. [3c] K. Maruyama, H. Tamiaki, T. Yanai, Bull. Chem. Soc. Jpn. 1985, 58, 781-782;
27. [3d] K. Maruyama, H. Tamiaki, J. Org. Chem. 1986, 51, 602-606;
28. [3e] K. Maruyama, H. Tamaki, S. Kawabata, J. Chem. Soc., Perkin Trans. 2 1986, 543-549;
29. [3f] K. Maruyama, H. Tamaki, J. Org. Chem. 1987, 52, 3967-3970;
30. [3g] G. Kaupp, H. Prinzbach, Justus Liebigs Ann. Chem. 1969, 725, 52-63;
31. [3h] S. Sakai, K. Ohkubo, F. Fujiwara, A. Ohyoshi, J. Mol. Cat. 1982, 16, 181;
32. [3i] K. Hirao, A. Yamashita, A. Ando, T. Hamada, O. Yonemitsu, J. Chem. Soc., Perkin. Trans. 1 1988, 2913-2916;
33. [3j] K. Hirao, A. Ando, T. Hamada, O. Yonemitsu, J. Chem. Soc., Chem. Commun. 1984, 300-302;
34. [3k] C. Kutal, J. Chem. Educ. 1983, 60, 882-887;
35. [3l] M. Irie, M. Kato, J. Am. Chem. Soc. 1985, 107, 1024-1028.
36. F. Starck, P. G. Jones, R. Herges, Eur. J. Org. Chem. 1998, 2533-2539.
37. Comprehensive Supramolecular Chemistry, Vol. 8: Physical Methods In Supramolecular Chemistry, 1st edition (Eds.: J. L. Atwood, J. E. D. Davies, D. MacNicol, F. Vögtle, J. M. Lehn, J. A. Ripmeester), Elsevier, Oxford, New York, Tokyo 1996, p. 463-464.
38. [6a] J. M. Timko, S. S. Moore, D. M. Walba, P. C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219;
39. [6b] S. S. Moore, T. L. Tarnowski, M. Newcomb, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 6398-6405.
40. K. H. Wong, H. L. Ng, J. Coord. Chem. 1981, 11, 49-55.
41. F. Köhler, R. Herges, MD Based Conformational Search, Christian-Albrechts-Universität Kiel, unpublished.
42. + complex of 12-crown-4.
43. For a review see: [10a] S. Shinkai, Bioorg. Chem. Front. 1990, 1, 162-193;
44. [10b] F. Vögtle, Supramolekulare Chemie, Teubner Verlag, Stuttgart 1989.
45. R. Herges, F. Starck, T. Winkler, M. Schmittel, Chem. Eur. J. 1999, 5, 2965-2969.