Templates, "wheeled reagents", and a new route to rotaxanes by anion complexation: The trapping method

Chemistry - A European Journal

Volumn 6, Issue 1, 2000, Pages 21-24

  Seel, Christian ^a   Vögtle, Fritz ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Host guest chemistry; Rotaxanes; Supramolecular chemistry; Template synthesis

Indexed keywords

ANION; CATENANE; ROTAXANE;

ARTICLE; CHEMISTRY; COMPLEX FORMATION; SYNTHESIS; TECHNIQUE;

EID: 0033982590     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000103)6:1<21::AID-CHEM21>3.0.CO;2-L     Document Type: Article

References (68)

1. a) H. L. Frisch, E. Wassermann, J. Am. Chem. Soc. 1961, 83, 3789-3795;
2. b) D. M. Walba, Tetrahedron 1985, 41, 3161-3212;
3. c) J.-C. Chambron, C. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162;
4. d) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064;
5. e) K. Mislow, Top. Stereochem. 1997, 22, 1-82.
6. G. Schul, A. Lüttringhaus, Angew. Chem. 1964, 76, 567-568;
7. Angew. Chem. Int. Ed. Engl. 1964, 3, 546-547;
8. G. Schul, Chem. Ber. 1967, 100, 2021-2037;
9. G. Schul, H. Zollenkopf, Liebigs. Ann. Chem. 1969, 721, 53-74.
10. I. T. Harrison, S. Harrison, J. Am. Chem. Soc. 1967, 89, 5723-5724;
11. I. T. Harrison, J. Chem. Soc. Perkin Trans. 1 1974, 301-304.
12. a) D. H. Busch, N. A. Stephenson, Coord. Chem. Rev. 1990, 100, 119-154;
13. b) S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469-475;
14. c) R. Hoss, F. Vögtle, Angew. Chem. 1994, 106, 389-398;
15. Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959;
16. d) Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, J.-P. Sauvage, M. W. Hosseini), Pergamon, Oxford, 1996;
17. e) Template Synthesis (Eds.: N. V. Gerbeleu, V.B. Arion, J. Burgess), Wiley, Chichester, 1999;
18. f) Templated Organic Synthesis (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1999;
19. g) T. J. Hubin, A. G. Kolchinski, A. L. Vance, D. H. Busch in Advances in Supramolecular Chemistry, vol. 5 (Ed.: G. W. Gokel), JAI Press, London, 1999, pp. 237-357.
20. M. C. Thompson, D. H. Busch, J. Am. Chem. Soc. 1962, 84, 1762-1763.
21. H. de Diesbach, E. von der Weid, Helv. Chim. Acta 1927, 10, 886-888.
22. C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 2495-2496.
23. J.-C. Chambron, J.-P. Sauvage, Chem. Eur. J. 1998, 4, 1362-1366, and references therein.
24. C. Wu, P. R. Lecavalier, Y. X. Shen, H. W. Gibson, Chem. Mater. 1991, 3, 569-572;
25. J.-C. Chambron, V. Heitz, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1992, 1131-1133.
26. D. B. Amabilino, J. F. Stoddart, Cheat. Rev. 1995, 95, 2725-2828.
27. For a neutral π-assembled system, see: D. G. Hamilton, J. E. Davies, L. Prodi, J. K. M. Sanders, Chem. Eur. J. 1998, 4, 608-620.
28. K. N. Houk, S. Menzer, S. P. Newton, F. M. Raymo, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1999, 121, 1479-1487.
29. P. L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani, M. Delgado, M. T. Gandolfi, T. T. Goodnow, A. E. Kaifer, D. Philp, M. Pietraszkiewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, J. Am. Chem. Soc. 1992, 114, 193-218.
30. First example: H. Ogino, J. Am. Chem. Soc. 1981, 103, 1303-1304.
31. S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078;
32. Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959.
33. For the molecules depicted, see: C. Seel, A. H. Parham, O. Safarowsky, G. M. Hübner, F. Vögtle, J. Org. Chem. 1999, 64, 7236-7242.
34. C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311.
35. F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631;
36. Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622.
37. First example: F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743.
38. A. G. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663;
39. D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756;
40. Angew. Chem. Int. Ed. Engl. 1997, 36, 752-756.
41. First example: A. G. Kolchinsky, D. H. Busch, N. W. Alcock, J. Chem. Soc. Chem. Commun. 1995, 1289-1291.
42. For related pseudorotaxanes, see: P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 2001-2004;
43. Angew. Chem. Int. Ed. Engl. 1995, 34, 1869-1872.
44. S. J. Loeb, J. A. Wisner, Chem. Commun. 1998, 2757-2758.
45. For general reviews on anion binding, see: B. Dietrich, Pure Appl. Chem. 1993, 65, 1457-1464;
46. C. Seel, A. Galán, J. de Mendoza, Top. Curr. Chem. 1995, 175, 101-132;
47. C. Seel, J. de Mendoza in Comprehensive Supramolecular Chemistry, Vol. 2 (Eds.: J. L. Atwood, J. E. D. Davies, D.D. MacNicol, F. Vögtle), Pergamon, Oxford, 1996, pp. 519-552;
48. K. T. Holman, J. L. Atwood, J. W. Steed in Advances in Supramolecular Chemistry, Vol 4 (Ed.: G. W. Gokel), JAI Press, London, 1997, pp. 287-330;
49. F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646;
50. The Supramolecular Chemistry of Anions (Ed.: A. Bianchi, K. Bowman-James, E. García-España), Wiley, Chichester, 1997.
51. G. M. Hübner, J. Gläser, C. Seel, F. Vögtle, Angew. Chem. 1999, 111, 395-398;
52. Angew. Chem. Int. Ed. 1999, 38, 383-386.
53. C. Reuter, W. Wienahd, G. M. Hübner, C. Seel, F. Vögtle, Chem. Eur. J. 1999, 5, 2692-2697;
54. G. M. Hübner, C. Reuter, C. Steel, F. Vögtle, Synthesis 1999, in press.
55. Selected papers: a) C. Gong, H. W. Gibson J. Am. Chem. Soc. 1997, 119, 8585-8591;
56. b) H. W. Gibson, D. S. Nagvekar, J. Powell, C. Gong, W. S. Bryant, Tetrahedron 1997, 53, 15197-15208;
57. c) C. Gong, T. E. Glass, H. W. Gibson Macromolecules 1998, 31, 308-313.
58. For recent reviews, see: References [1c], [4d], [10]; H. W. Gibson in Large Ring Molecules (Ed.: J. A. Semlyen), Wiley, Chichester, 1996, pp. 191-262;
59. R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980;
60. Angew. Chem. Int. Ed. Engl. 1997, 56, 930-944;
61. Catenanes, Rotaxanes, Knots (Ed.: J.-P. Sauvage), VCH-Wiley, Weinheim; in press.
62. Not all of the reported syntheses are template-directed, see, for example: References [2] and [3]; G. Agam, D. Graiver, A. Zilkha, J. Am. Chem. Soc. 1976, 98, 5206-5214;
63. D. M. Walba, R. M. Richards, R. C. Haltiwanger, J. Am. Chem. Soc. 1982, 104, 3219;
64. M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250;
65. Angew. Chem. Int. Ed. Engl. 1997, 36, 1199-1201;
66. D. B. Amabilino, M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradsky, A. Credi, M. Higuchi, F. M. Raymo, T. Shimizu, J. F. Stoddart, M. Venturi, K. Yase, New J. Chem. 1998, 959-972.
67. For a catenane synthesized from preformed metallamacrocycles under thermodynamic template assistance, see: M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612;
68. N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796.