Synthesis of catenane structures via ring-closing metathesis

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5463-5471

  Weck, Marcus ^a   Mohr, Bernhard ^b   Sauvage, Jean Pierre ^b   Grubbs, Robert H ^a  

^a California Institute of Technology ^*  (United States)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; HYDROGENATION; HYDROLYSIS; OXIDATION; SYNTHESIS;

EID: 0033597874     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990268c     Document Type: Article

References (129)

1. For some recent reviews of interlocked and intertwined structures, see: (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (d) Chambron, J.-C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 132. (e) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J. C. In Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 9, p 43. (f) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1996, 148, 249. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451. (h) Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911. (i) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (j) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
2. For some recent reviews of interlocked and intertwined structures, see: (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (d) Chambron, J.-C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 132. (e) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J. C. In Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 9, p 43. (f) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1996, 148, 249. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451. (h) Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911. (i) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (j) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
3. For some recent reviews of interlocked and intertwined structures, see: (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (d) Chambron, J.-C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 132. (e) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J. C. In Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 9, p 43. (f) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1996, 148, 249. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451. (h) Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911. (i) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (j) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
4. For some recent reviews of interlocked and intertwined structures, see: (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (d) Chambron, J.-C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 132. (e) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J. C. In Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 9, p 43. (f) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1996, 148, 249. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451. (h) Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911. (i) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (j) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
5. For some recent reviews of interlocked and intertwined structures, see: (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (d) Chambron, J.-C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 132. (e) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J. C. In Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 9, p 43. (f) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1996, 148, 249. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451. (h) Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911. (i) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (j) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
6. For some recent reviews of interlocked and intertwined structures, see: (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (d) Chambron, J.-C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 132. (e) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J. C. In Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 9, p 43. (f) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1996, 148, 249. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451. (h) Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911. (i) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (j) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
7. For some recent reviews of interlocked and intertwined structures, see: (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (d) Chambron, J.-C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 132. (e) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J. C. In Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 9, p 43. (f) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1996, 148, 249. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451. (h) Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911. (i) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (j) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
8. For some recent reviews of interlocked and intertwined structures, see: (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (d) Chambron, J.-C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 132. (e) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J. C. In Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 9, p 43. (f) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1996, 148, 249. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451. (h) Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911. (i) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (j) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
9. For some recent reviews of interlocked and intertwined structures, see: (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (d) Chambron, J.-C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 132. (e) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J. C. In Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 9, p 43. (f) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1996, 148, 249. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451. (h) Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911. (i) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (j) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
10. For some recent reviews of interlocked and intertwined structures, see: (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (d) Chambron, J.-C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 132. (e) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J. C. In Comprehensive Supramolecular Chemistry; Pergamon Press: Oxford, 1996; Vol. 9, p 43. (f) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1996, 148, 249. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451. (h) Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911. (i) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (j) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
11. (a) Lehn, J. M. Supramolecular Chemistry; VCH: Weinheim, 1995; and references therein.
12. (b) Balzani, V.; De Cola, L. Supramolecular Chemistry; Kluwer Academic Publishers: Dordrecht, 1992; and references therein.
13. (c) Lehn, J. M. Angew. Chem., Int. Ed. Engl. 1988, 27, 89.
14. (d) Ringsdorf, H.; Schlarb, V.; Venzmer, J. Angew. Chem., Int. Ed. Engl. 1988, 27, 113.
15. (e) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37.
16. The nomenclature employed in these systems involves placing (in square brackets) the number of the components before the name of the compounds. Therefore, a [2]catenane is comprised of two interlocked macrocycles.
17. Schill, G. Catenanes, Rotaxanes and Knots; Academic Press: New York, 1971.
18. (a) Frisch, H. L.; Wassermann, E. J. Am. Chem. Soc. 1961, 83, 3789.
19. (b) Ben-Efraim, D. A.; Batich, C.; Wasaerman, E. J. Am. Chem. Soc. 1970, 92, 2132.
20. (a) Livoreil, A.; Sauvage, J.-P.; Armaroli, N.; Balzani, V.; Flamigni, L.; Ventura, B. J. Am. Chem. Soc. 1997, 119, 12114.
21. (b) Cárdenas, D. J.; Gaviña, P.; Sauvage, J.-P. J. Am. Chem. Soc. 1997, 119, 2656.
22. (c) Dietrich-Buchecker, C.; Sauvage, J.-P. Tetrahedron 1990, 46, 503.
23. (d) Nierengarten, J.-F.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. J. Am. Chem. Soc. 1994, 116, 375.
24. (e) Collin, J.-P.; Gaviña, P.; Sauvage, J.-P. J. Chem. Soc., Chem. Commun. 1996, 2005.
25. (f) Baumann, F.; Livoreil, A.; Kaim, W.; Sauvage, J.-P. J. Chem. Soc., Chem. Commun. 1997, 35.
26. (g) Chambron, J.-C.; Dietrich-Buchecker, C.; Nierengarten, J.-F.; Sauvage, J.-P.; Solladié, N.; Albrecht-Gary, A.-M.; Meyer, M. New J. Chem. 1995, 19, 409.
27. (h) Dietrich-Buchecker, C.; Leize, E.; Nierengarten, J.-F.; Sauvage, J.-P.; Dorsselaer, A. V. J. Chem. Soc., Chem. Commun. 1994, 2257.
28. (i) Livoreil, A.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. J. Am. Chem. Soc. 1994, 116, 9399.
29. (j) Dietrich-Buchecker, C. O.; Guilhem, J.; Kern, J.-M.; Pascard, C.; Sauvage, J.-P. Inorg. Chem. 1994, 33, 3498.
30. (k) Chambron, J.-C.; Mitchell, D. K.; Sauvage, J.-P. J. Am. Chem. Soc. 1992, 114, 4625.
31. (l) Dietrich-Buchecker, C.; Sauvage, J.-P.; Kern, J.-M. J. Am. Chem. Soc. 1989, 111, 7791.
32. (m) Cesario, M.; Dietrich-Buchecker, C. O.; Guilhem, J.; Pascard, C.; Sauvage, J.-P. J. Chem. Soc., Chem. Commun. 1985, 244.
33. (n) Dietrich-Buchecker, C.; Sauvage, J.-P. Tetrahedron Lett. 1983, 24, 5091.
34. (o) Dietrich-Buchecker, C.; Sauvage, J.-P.; Kern, J.-M. J. Am. Chem. Soc. 1984, 106, 3043.
35. (a) Dietrich-Buchecker, C. O.; Nierengarten, J.-F.; Sauvage, J.-P.; Armaroli, N.; Balzani, V.; DeCola, L. J. Am. Chem. Soc. 1993, 115, 11237.
36. (b) Carina, R. F.; Dietrich-Buchecker, C.; Sauvage, J.-P. J. Am. Chem. Soc. 1996, 118, 9110.
37. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P.; DeCian, A.; Fischer, J. J. Chem. Soc., Chem. Commun. 1994, 2231.
38. (d) Dietrich-Buchecker, C. O.; Nierengarten, J.-F.; Sauvage, J.-P. Tetrahedron Lett. 1992, 33, 3625.
39. (e) Dietrich-Buchecker, C. O.; Sauvage, J.-P.; Kintzinger, J.-P.; Maltèse, P.; Pascard, C.; Guilhelm, J. New. J. Chem. 1992, 16, 931.
40. (f) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Angew. Chem., Int. Ed. Engl. 1989, 28, 8, 189.
41. (a) Kern, J.-M.; Sauvage, J.-P.; Bidan, G.; Bilon, M.; Divisa-Blohorn, B. Adv. Mater. 1996, 8, 580.
42. (b) Chambron, J.-C.; Sauvage, J.-P. Chem. Eur. J. 1998, 4, 1362.
43. (a) Ashton, P. R.; Chrystal, E. J. T.; Glink, P. T.; Menzer, S.; Schiavo, C.; Spencer, N.; Stoddart, J. F.; Tasker, P. A.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 709.
44. (b) Ashton, P. R.; Baxter, I.; Cantrill, S. J.; Fyfe, M. C. T.; Glink, P. T.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1294.
45. (c) Ashton, P. R.; Baxter, I.; Fyfe, M. C. T.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 2297.
46. (d) Ashton, P. R.; Ballaedini, R.; Balzani, V.; Gómez-López, M.; Lawrence, S. E.; Martíne-Díaz, M. V.; Montalti, M.; Piersanti, A.; Prodi, L.; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1997, 119, 10641.
47. (e) Ashton, P. R.; Collins, A. N.; Fyfe, M. C. T.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 735.
48. (f) Ashton, P. R.; Glink, P. T.; Stoddart, J. F.; Tasker, P. A.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 729.
49. (g) Ashton, P. R.; Chrystal, E. J. T.; Glink, P. T.; Menzer, S.; Schiavo, C.; Stoddart, J. F.; Tasker, P. A.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1869.
50. (h) Ashton, P. R.; Campbell, P. J.; Chrystal, E. J. T.; Glink, P. T.; Menzer, S.; Philp, D.; Spencer, N.; Stoddart, J. F.; Tasker, P. A.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1865.
51. (i) Ashton, P. R.; Fyfe, M. C. T.; Glink, P. T.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1997, 119, 12514.
52. (a) Anelli, P. L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M. T.; Goodnow, T. T.; Kaifer, A. E.; Philp, D.; Pietraszkiewicz, M.; Prodi, L.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. J. Am. Chem. Soc. 1992, 114, 193.
53. (b) Amabilino, D. B.; Ashton, P. R.; Brown, C. L.; Córdova, E.; Godínez, L. A.; Goodnow, T. T.; Kaifer, A. E.; Newton, S. P.; Pietraszkiewicz, M.; Philp, D.; Raymo, F. M.; Reder, A. S.; Rutland, M. T.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 1271.
54. (c) Ashton, P. R.; Joachimi, D.; Spencer, N.; Stoddart, J. F.; Tschierske, C.; White, A. J. P.; Williams, D. J.; Zab, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1503.
55. (d) Amabilino, D. B.; Ashton, P. R.; Pérez-Garcia, L.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 2378.
56. (e) Asakawa, M.; Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Menzer, S.; Pasini, D.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J.; Wyatt, P. G. Chem. Eur. J. 1997, 3, 463.
57. (f) Anelli, P.-L.; Asakawa, M.; Ashton, P. R.; Bissell, R. A.; Clavier, G.; Górski, R.; Kaifer, A. E.; Langford, S. J.; Mattersteig, G.; Menzer, S.; Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Williams, D. J. Chem. Eur. J. 1997, 3, 1113.
58. (g) Ashton, P. R.; Horn, T.; Menzer, S.; Preece, J. A.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Synthesis 1997, 481.
59. (h) Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Mattersteig, G.; Matthews, O. A.; Montalti, O. A.; Spencer, N.; Stoddart, J. F.; Venturi, M. Chem. Eur. J. 1997, 3, 1992.
60. (i) Gillard, R. E.; Raymo, F. M.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 1933.
61. (j) Ashton, P. R.; Boyd, S. E.; Menzer, S.; Pasini, D.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; White, A. J. P.; Williams, D. J.; Wyatt, P. G. Chem. Eur. J. 1998, 4, 299.
62. (k) Amabilino, D. B.; Stoddart, J. F.; Williams, D. J. Chem. Mater. 1994, 6, 1159.
63. (l) Menzer, S.; White, A. J. P.; Williams, D. J.; Belohradsky, M.; Hamers, C.; Raymo, F. M.; Shipway, A. N.; Stoddart, J. F. Macromolecules 1998, 31, 295.
64. (m) Amabilino, D. B.; Ashton, P. R.; Balzani, V.; Boyd, S. E.; Credi, A.; Lee, J. Y.; Menzer, S.; Stoddart, J. F.; Venturi, M.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 4295.
65. (a) Fischer, C.; Nieger, M.; Mogck, O.; Böhmer, V.; Ungaro, R.; Vögtle, F. Eur. J. Org. Chem. 1998, 155.
66. (b) Dünnwald, T.; Jäger, R.; Vögtle, F. Chem. Eur. J. 1997, 3, 2043.
67. (c) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303.
68. (d) Carver, F. J.; Hunter, C. A.; Shannon, R. J. J. Chem Soc., Chem. Commun. 1994, 1277.
69. (a) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092.
70. (b) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306.
71. (c) Leigh, D. A.; Murphy, A.; Smart, J. P.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 728.
72. (e) Johnston, A. G.; Leigh, D. A.; Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209.
73. (a) Wenz, G.; Steinbrunn, M. B.; Landfester, K. Tetrahedron 1997, 53, 15575.
74. (b) Herrmann, W.; Schneider, M.; Wenz, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2511.
75. (c) Ogino, H. J. Am. Chem. Soc. 1981, 103, 1303.
76. (d) Harada, A.; Li, J.; Kamachi, M. Nature 1992, 356, 325.
77. (a) Gibson, H. W.; Liu, S.; Gong, C.; Ji, Q.; Joseph, E. Macromolecules 1997, 30, 3711.
78. (b) Gong, C.; Gibson, H. W. J. Am. Chem. Soc. 1997, 119, 5862.
79. (c) Gong, C.; Gibson, H. W. J. Am. Chem. Soc. 1997, 119, 8585.
80. (d) Gibson, H. W.; Nagvekar, D. S.; Powell, J.; Gong, C.; Bryant, W. S. Tetrahedron 1997, 53, 15197.
81. (e) Gong, C.; Gibson, H. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 2331.
82. (f) Gong, C.; Gibson, H. W. Angew. Chem., Int. Ed. Engl. 1998, 37, 310.
83. (g) Gong, C.; Glass, T. E.; Gibson, H. W. Macromolecules 1998, 31, 308.
84. (a) Hamilton, D. G.; Feeder, N.; Prodi, L.; Teat, S. J.; Clegg, W.; Sanders, J. K. M. J. Am. Chem. Soc. 1998, 120, 1096.
85. (b) Hamilton, D. G.; Davies, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608.
86. (a) Fujita, M.; Ogura, K. Bull. Chem. Soc. Jpn. 1996, 69, 1471.
87. (b) Fujita, M.; Aoyagi, M.; Ibukuro, F.; Ogura, K.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 611.
88. Whang, D.; Park, K-M.; Heo, J.; Ashton, P.; Kim, K. J. Am. Chem. Soc. 1998, 120, 0, 4899.
89. Rowan, A. E.; Aarts, P. P. M.; Koutstaal, K. W. M. J. Chem. Soc., Chem. Commun. 1998, 611.
90. Kaes, C.; Hosseini, M. W.; Rickard, C. E. F.; Skelton, B. W.; White, A. H. Angew. Chem., Int. Ed. Engl. 1998, 37, 920.
91. Zhu, S. S.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 12568.
92. Anderson, S.; Claridge, T. D. W.; Anderson, H. L. Angew. Chem., Int. Ed. Engl. 1997, 36, 1310.
93. Schmittel, M.; Ganz, A. J. Chem. Soc., Chem. Commun. 1997, 999.
94. Kolchinsi, A. G.; Busch, D. H.; Alcock, N. W. J. Chem. Soc., Chem. Commun. 1995, 1289.
95. Owen, G. J.; Hodge, P. J. Chem. Soc., Chem. Commun. 1997, 11.
96. Gruter, G.-J. M.; Akkerman, O. S.; Bickelhaupt, F. Tetrahedron 1996, 52, 2565.
97. Mingos, D. M. P.; Yau, J.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894.
98. Benniston, A. C.; Mackie, P. R.; Harriman, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 7, 354.
99. Meschke, C.; Buschmann, H.-J.; Schollmeyer, E. Macromol. Rapid Commun. 1998, 19, 59.
100. (a) Chambron, J.-C.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1993, 115, 7419.
101. (b) Harriman, A.; Sauvage, J.-P. Chem. Soc. Rev. 1996, 41.
102. (a) Fujita, M.; Ibukura, F.; Hajihara, H.; Ogura, K. Nature 1994, 367, 720.
103. (b) Whang, D. M.; Park, K. M.; Heo, J.; Ashton, P.; Kim, K. J. Am. Chem. Soc. 1998, 120, 4899.
104. For early attempts to synthesize catenanes via RCM, see: Wolovsky, R. J. Am. Chem. Soc. 1970, 92, 2132.
105. For recent reviews on RCM, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (d) Chang, S.; Grubbs, R. H. Tetrahedron 1998, 54, 4413. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
106. For recent reviews on RCM, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (d) Chang, S.; Grubbs, R. H. Tetrahedron 1998, 54, 4413. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
107. For recent reviews on RCM, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (d) Chang, S.; Grubbs, R. H. Tetrahedron 1998, 54, 4413. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
108. For recent reviews on RCM, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (d) Chang, S.; Grubbs, R. H. Tetrahedron 1998, 54, 4413. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
109. For recent reviews on RCM, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (d) Chang, S.; Grubbs, R. H. Tetrahedron 1998, 54, 4413. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
110. (a) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 3974.
111. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
112. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 5426.
113. (a) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606.
114. (b) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942.
115. (c) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364.
116. (d) König, B.; Horn, C. Synlett 1996, 1013.
117. (e) Fürstner, A.; Kindler, N. Terahedron Lett. 1996, 37, 7005.
118. (f) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000.
119. (g) Xu, Z.; Johannes, C. H.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926.
120. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1998, 35, 2399.
121. (i) Fürstner, A.; Langemann, K. Synthesis 1997, 792.
122. Mohr, B.; Weck, M.; Sauvage, J.-P.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1308.
123. 36 Sauvage et al. synthesized a molecular knot using RCM: Dietrich-Buchecker, C.; Rapenne, G.; Sauvage, J.-P. J. Chem. Soc., Chem. Commun. 1997, 2053.
124. For other catenane systems cyclized via RCM, see: (a) Hamilton, D. G.; Feeder, N.; Teat, S. J.; Sanders, J. K. M. New. J. Chem. 1998, 1019. (b) Kidd, T. J.; Leigh, D. A.; Wilson, A. J. J. Am. Chem. Soc. 1999, 121, 1599.
125. For other catenane systems cyclized via RCM, see: (a) Hamilton, D. G.; Feeder, N.; Teat, S. J.; Sanders, J. K. M. New. J. Chem. 1998, 1019. (b) Kidd, T. J.; Leigh, D. A.; Wilson, A. J. J. Am. Chem. Soc. 1999, 121, 1599.
126. Vetter, W.; Logemann, E.; Schill, G. Org. Mass. Spectrom. 1977, 12, 351.
127. Marsella, M. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1101.
128. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
129. These interactions have been observed in the solid state for structurally related [2]catenates (see ref 6j,m).