Reinvestigation of supramolecular complexes with cyclophanes of the Stetter and Koga type: Agreement and disagreement with solid-state structures

European Journal of Organic Chemistry

Volumn , Issue 20, 2009, Pages 3450-3453

  Wald, Peter ^a   Schneider, Hans Jörg ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Cyclophanes; NMR spectroscopy; Supramolecular chemistry

Indexed keywords

EID: 67650485760     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900384     Document Type: Article

References (60)

1. A. Lüttringhaus, Justus Liebigs Ann. Chem. 1937, 528, 181;
2. A. Lüttringhaus, Justus Liebigs Ann. Chem. 1937, 528, 211;
3. A. Lüttringhaus, Justus Liebigs Ann. Chem, 1937, 528, 223;
4. K. Ziegler, A. Lüttringhaus, Justus Liebigs Ann, Chem. 1934, 511, 1;
5. a small cyclophane was already described in 1899: M. Pellegrin, Recueil Trav. Chim. Pays Bas 1899, 18, 457.
6. First cyclophane report by D. J. Cram.: D. J. Cram, H. Steinberg, J. Am. Chem. Soc. 1951, 73, 5691.
7. F. Diederich, Cyclophanes, RSC, Cambridge, UK, 1991;
8. R. Gleiter, H. Hopf, Modern Cyclophane Chemistry, Wiley-VCH, Weinheim, 2004;
9. D. J. Cram, J. M. Cram, Acc. Chem. Res. 1971, 4, 204;
10. F. Diederich, Angew. Chem. 1988, 100, 372-396;
11. E. Weber (Ed.), Topics in Current Chemistry Vol. 172: Cyclophanes, Springer, Berlin, 1994;
12. F. Vögtle (Ed.), Topics in Current Chemistry Vol. 115: Cyclophanes II, Springer, Berlin, 1983;
13. F. Vögtle (Ed.), Topics in Current Chemistry Vol. 113: Cyclophanes I, Springer, Berlin, 1983;
14. B. König, Top. Curr. Chem. 1998, 196, 91-136;
15. H. Hopf, Tetrahedron 2008, 64, 11504;
16. J. O. Jeppesen, M. B. Nielsen, J Becher, Chem. Rev. 2004, 104, 5115 (tetrathiafulvalene cyclophanes).
17. W. L. Jorgensen, T. B. Nguyen, E. M. Sanford, I. Chao, K. N. Houk, F. Diederich, J. Am. Chem. Soc. 1992, 114, 4003;
18. T. Z. M. Denti, W F. van Gunsteren, F. Diederich, J. Am. Chem. Soc. 1996, 118, 6044;
19. C. E. Chang, M. K. Gilson, J. Am. Chem. Soc. 2004, 126, 13156;
20. S. B. Ferguson, E. M. Seward, F. Diederich, E. M. Sanford, A. Chou, P. Inocencioszweda, C. B. Knobler, J. Org. Chem, 1988, 53, 5593;
21. S. Kunsagi-Mate, K. Szabo, I. Bitter, G. Nagy, L. Kollar, J. Phys. Chem. A 2005, 109, 5237;
22. S. Grimme, Chem, Eur. J. 2004, 10, 3423-3429;
23. G. F Caramori, S. E. Galembeck, J. Phys. Chem. A 2008, 112, 11784;
24. G. Ercolani, P. Mencarelli, J. Org. Chem. 2003, 68, 6470.
25. For recent applications, see: T Masuko, T. Kusama, R. Namiki, K. Metori, Y Kizawa, M. Miyake, Chem. Pharm. Bull. 2009, 57, 95;
26. A. A. Karasik, D. V Kulikov, A. S. Balueva, S. N. Ignat'eva, O. N. Kataeva, P. Lonnecke, A. V. Kozlov, S. K. Latypov, E. Hey-Hawkins, O. G. Sinyashin, P, N-Containing cyclophanes with large helical hydrophobic cavities: prospective precursors for the design of a molecular reactor, Dalton Trans. 2009, 490
27. M. V. Baker, D. H. Brown, C. H. Heath, B. W Skelton, A. H. White, C. C. Williams, J. Org. Chem. 2008, 73, 9340;
28. M. Arunachalam, I. Ravikumar, P. Ghosh, J. Org. Chem. 2008, 73, 9144;
29. D. B. Werz, F. R. Fischer, S. C. Kornmayer, F. Rominger, R. Gleiter, J. Org. Chem. 2008, 73, 8021;
30. J. Yan, Y. C. Zhou, P. Yu, L. Su, L. Q. Mao, D. Q. Zhang, D. B. Zhu, Chem. Commun. 2008, 4330;
31. N. Bogdan, E. Condamine, L. Toupet, Y. Ramondenc, E. Bogdan, I. Grosu, J. Org. Chem. 2008, 73, 5831;
32. P. I. Dron, S. Fourmentin, F. Cazier, D. Landy, G. Surpateanu, Supramol. Chem. 2008, 20, 473;
33. S. O. Kang, V. W. Day, K. Bowman-James, Org. Lett. 2008, 10, 2677;
34. K. Raatikainen, J. Huuskonen, E. Kolehmainen, K. Rissanen, Chem. Eur. J. 2008, 14, 3297;
35. O. Hayashida, D. Sato, J. Org. Chem. 2008, 73, 3205;
36. C. Virues, R. E. Navarro, E. F. Velazquez, M. Inoue, Supramol. Chem. 2008, 20, 301;
37. H. T. Xi, X. Q. Sun, Q. Meng, Y. Pan, H. W. Hu, Prog. Chem. 2008, 20, 87;
38. Y. Morisaki, Y. Chujo, Prog. Polym. Sci. 2008, 33, 346;
39. M. Shibahara, M. Watanabe, T. Iwanaga, T. Matsumoto, K. Ideta, T. Shinmyozu, J. Org. Chem. 2008, 73, 4433.
40. H.-J. Schneider, T. Blatter, S. Simova, I. Theis, J. Chem. Soc., Chem. Commun. 1989, 580.
41. H.-J. Schneider, T. Blatter, Angew. Chem. 1988, 100, 1211;
42. Angew. Chem. Int. Ed. Engl. 1988, 27, 1163.
43. C. Davies, L. Ren, R. Gustafson, T. Buthelezi, R. A. Bartsch, M. Surowiec, J. Inch Phenom. Macrocycl. Chem. 2008, 61, 347;
44. R. Castro, P. D. Davidov, K. A. Kumar, A. P. Marchand, J. D. Evanseck, A. E. Kaifer, J. Phys. Org. Chem. 1997, 10, 369;
45. K. Saigo, M. Kubo, R. J. Lin, A. Youda, M. Hasegawa, Tetrahedron Lett. 1985, 26, 1325.
46. H. Stetter, E. E. Roos, Chem. Ber. 1955, 88, 1390.
47. K. Odashima, A. Itai, Y. Iitaka, Y. Arata, K. Koga, Tetrahedron Lett. 1980, 21, 4347.
48. R. Hilgenfeld, W Saenger, Angew. Chem. 1982, 94, 788;
49. Angew. Chem, Int. Ed. Engl. 1982, 21, 1690.
50. D. Bogdan, E. Condamine, L. Toupet, Y Ramondenc, I. Silaghi- Dumitrescu, I. Grosu, Tetrahedron Lett. 2008, 49, 5204, and references therein.
51. K. Odashima, A. Itai, Y. Iitaka, Y. Arata, K. Koga, J. Org. Chem, 1985, 50, 4478.
52. H.-J. Schneider, R. Kramer, S. Simova, U. Schneider, J. Am. Chem, Soc. 1988, 110, 6442.
53. H.-J. Schneider, Angew. Chem. 1991, 103, 1419;
54. Angew. Chem. Int. Ed. Engl. 1991, 30, 1417;
55. H.-J. Schneider, I. Theis, Angew. Chem. 1989, 101, 757;
56. Angew. Chem. Int. Ed. Engl. 1989, 28, 753.
57. H.-J. Schneider, T. Blatter, B. Palm, U. Pfingstag, V. Rüdiger, I. Theis, J. Am. Chem. Soc. 1992, 114, 7704.
58. H.-J. Schneider, Angew. Chem. 2009, 121, 3982-4036;
59. Angew. Chem. Int. Ed. 2009, 48, 3924-3977.
60. A. K. Shestakova, V A. Chertkov, H.-J. Schneider, Tetrahedron Lett. 2000, 41, 6753.