[1]Rotaxanes and pretzelanes: Synthesis, chirality, and absolute configuration

Chemistry - A European Journal

Volumn 6, Issue 9, 2000, Pages 1674-1682

  Reuter, Carin ^a   Mohry, André ^a   Sobanski, Adam ^a   Vögtle, Fritz ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Catenanes; Chirality; Cycloenantiomerism; Enantiomeric resolution; Rotaxanes; Supramolecular chemistry

Indexed keywords

CATENANE; PRETZELANE; ROTAXANE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034595338     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000502)6:9<1674::AID-CHEM1674>3.3.CO;2-9     Document Type: Article

References (73)

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2. H. L. Frisch, E. Wassermann, J. Am. Chem. Soc. 1961, 83, 3789-3795; V. Prelog, H. Gerlach, Helv. Chim. Acta 1964, 47, 2288-2294; H. Gerlach, J. A. Owtschinnikow, Helv. Chim. Acta 1964, 47, 2294-2302; R. Cruse in, Stereochemie der Kohlenstoffverbindungen (Ed.: E. L. Eliel), VCH, Weinheim, Germany, 1966.
3. H. L. Frisch, E. Wassermann, J. Am. Chem. Soc. 1961, 83, 3789-3795; V. Prelog, H. Gerlach, Helv. Chim. Acta 1964, 47, 2288-2294; H. Gerlach, J. A. Owtschinnikow, Helv. Chim. Acta 1964, 47, 2294-2302; R. Cruse in, Stereochemie der Kohlenstoffverbindungen (Ed.: E. L. Eliel), VCH, Weinheim, Germany, 1966.
4. H. L. Frisch, E. Wassermann, J. Am. Chem. Soc. 1961, 83, 3789-3795; V. Prelog, H. Gerlach, Helv. Chim. Acta 1964, 47, 2288-2294; H. Gerlach, J. A. Owtschinnikow, Helv. Chim. Acta 1964, 47, 2294-2302; R. Cruse in, Stereochemie der Kohlenstoffverbindungen (Ed.: E. L. Eliel), VCH, Weinheim, Germany, 1966.
5. For topologically chiral catenanes, see: a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511 b) K. Mislow, Top. Stereochem. 1999, 1-82 c) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064 c) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162 d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212 e) C-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660 f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T.-J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine, New York, 1996 g) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Köhler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851.
6. For topologically chiral catenanes, see: a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511 b) K. Mislow, Top. Stereochem. 1999, 1-82 c) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064 c) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162 d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212 e) C-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660 f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T.-J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine, New York, 1996 g) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Köhler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851.
7. For topologically chiral catenanes, see: a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511 b) K. Mislow, Top. Stereochem. 1999, 1-82 c) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064 c) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162 d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212 e) C-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660 f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T.-J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine, New York, 1996 g) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Köhler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851.
8. For topologically chiral catenanes, see: a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511 b) K. Mislow, Top. Stereochem. 1999, 1-82 c) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064 c) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162 d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212 e) C-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660 f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T.-J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine, New York, 1996 g) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Köhler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851.
9. For topologically chiral catenanes, see: a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511 b) K. Mislow, Top. Stereochem. 1999, 1-82 c) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064 c) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162 d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212 e) C-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660 f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T.-J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine, New York, 1996 g) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Köhler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851.
10. For topologically chiral catenanes, see: a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511 b) K. Mislow, Top. Stereochem. 1999, 1-82 c) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064 c) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162 d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212 e) C-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660 f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T.-J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine, New York, 1996 g) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Köhler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851.
11. For topologically chiral catenanes, see: a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511 b) K. Mislow, Top. Stereochem. 1999, 1-82 c) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064 c) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162 d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212 e) C-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660 f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T.-J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine, New York, 1996 g) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Köhler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851.
12. For topologically chiral catenanes, see: a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511 b) K. Mislow, Top. Stereochem. 1999, 1-82 c) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064 c) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162 d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212 e) C-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660 f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T.-J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine, New York, 1996 g) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Köhler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851.
13. For topologically chiral catenanes, see: a) K. Mislow, Croat. Chem. Acta 1996, 69, 485-511 b) K. Mislow, Top. Stereochem. 1999, 1-82 c) D. K. Mitchell, J.-C. Chambron, J. Chem. Educ. 1995, 72, 1059-1064 c) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Top. Curr. Chem. 1993, 165, 131-162 d) D. M. Walba, Tetrahedron 1985, 41, 3161-3212 e) C-T. Chen, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. 1995, 107, 2870-2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660 f) N. C. Seeman, H. Wang, J. Qi, X. Li, Y. Wang, H. Qui, B. Liu, Z. Shen, W. Sun, F. Liu, J. J. Molenda, S. M. Du, J. Chen, J. E. Mueller, Y. Zhang, T.-J. Fu, S. Zhang, Biological Structure and Dynamics, Adenine, New York, 1996 g) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Köhler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851.
14. a) G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York and London, 1971;
15. For chiral [2]rotaxanes, see b) P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908 c) A. Archut, W. M. Müller, S. Baumann, M. Habel, F. Vögtle, Liebigs Ann. Chem. 1997, 495-499 d) P. R. Ashton, S. R. L. Everitt, M. Gómez-López, N. Jaymaran, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 5691-5694 e)T. Schmidt, R. Schmieder, W. M. Müller, B. Kiupel, F. Vögtle, Eur. J. Org. Chem. 1998, 2003-2007 f) M. Asakawa, H. M. Janssen, E. W. Meijer, D. Pasini, J. F. Stoddart, Eur. J. Org. Chem. 1998, 983-986.
16. For chiral [2]rotaxanes, see b) P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908 c) A. Archut, W. M. Müller, S. Baumann, M. Habel, F. Vögtle, Liebigs Ann. Chem. 1997, 495-499 d) P. R. Ashton, S. R. L. Everitt, M. Gómez-López, N. Jaymaran, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 5691-5694 e)T. Schmidt, R. Schmieder, W. M. Müller, B. Kiupel, F. Vögtle, Eur. J. Org. Chem. 1998, 2003-2007 f) M. Asakawa, H. M. Janssen, E. W. Meijer, D. Pasini, J. F. Stoddart, Eur. J. Org. Chem. 1998, 983-986.
17. For chiral [2]rotaxanes, see b) P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908 c) A. Archut, W. M. Müller, S. Baumann, M. Habel, F. Vögtle, Liebigs Ann. Chem. 1997, 495-499 d) P. R. Ashton, S. R. L. Everitt, M. Gómez-López, N. Jaymaran, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 5691-5694 e)T. Schmidt, R. Schmieder, W. M. Müller, B. Kiupel, F. Vögtle, Eur. J. Org. Chem. 1998, 2003-2007 f) M. Asakawa, H. M. Janssen, E. W. Meijer, D. Pasini, J. F. Stoddart, Eur. J. Org. Chem. 1998, 983-986.
18. For chiral [2]rotaxanes, see b) P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908 c) A. Archut, W. M. Müller, S. Baumann, M. Habel, F. Vögtle, Liebigs Ann. Chem. 1997, 495-499 d) P. R. Ashton, S. R. L. Everitt, M. Gómez-López, N. Jaymaran, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 5691-5694 e)T. Schmidt, R. Schmieder, W. M. Müller, B. Kiupel, F. Vögtle, Eur. J. Org. Chem. 1998, 2003-2007 f) M. Asakawa, H. M. Janssen, E. W. Meijer, D. Pasini, J. F. Stoddart, Eur. J. Org. Chem. 1998, 983-986.
19. For chiral [2]rotaxanes, see b) P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 899-908 c) A. Archut, W. M. Müller, S. Baumann, M. Habel, F. Vögtle, Liebigs Ann. Chem. 1997, 495-499 d) P. R. Ashton, S. R. L. Everitt, M. Gómez-López, N. Jaymaran, J. F. Stoddart, Tetrahedron Lett. 1997, 38, 5691-5694 e)T. Schmidt, R. Schmieder, W. M. Müller, B. Kiupel, F. Vögtle, Eur. J. Org. Chem. 1998, 2003-2007 f) M. Asakawa, H. M. Janssen, E. W. Meijer, D. Pasini, J. F. Stoddart, Eur. J. Org. Chem. 1998, 983-986.
20. a) D. K. Mitchell, J.-P. Sauvage, Angew. Chem. 1988, 100, 985-987 Angew. Chem. Int. Ed. Engl. 1988, 27, 930-931
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22. b) J.-F. Nierengarten, C. O. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1994, 116, 375-376;
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29. a) Cycloenantiomerism was first discussed in the case of cyclopeptides, in which it depends on both the ring direction and on the distribution pattern of the stereogenic centers in the already centrochiral amino acid units: see ref. [2] and also M. Chorev, M. Goodman, Acc. Chem. Res. 1979,12, 1-7; K. Mislow, Chimia 1986, 40, 395-402
30. a) Cycloenantiomerism was first discussed in the case of cyclopeptides, in which it depends on both the ring direction and on the distribution pattern of the stereogenic centers in the already centrochiral amino acid units: see ref. [2] and also M. Chorev, M. Goodman, Acc. Chem. Res. 1979,12, 1-7; K. Mislow, Chimia 1986, 40, 395-402
31. b) For cycloenantiomerism of topology, see ref. [3]:see also: V. I. Sokolov, Russ. Chem. Rev. 1973, 42, 452-455
32. c) see also: J. Wermuth, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1997, 119, 1328-1335, and references cited therein.
33. R. Jäger, M. Händel, J. Harren, K. Rissanen, F. Vögtle, Liebigs Ann. Chem. 1996, 1201-1207.
34. a) S. Ottens-Hildebrandt, T. Schmidt, J. Harren, F. Vögtle, Liebigs Ann. Chem. 1995, 1855-1860
35. b) F. Vögtle, T. Dünnwald, T. Schmidt, Acc. Chem. Res. 1996, 29, 451-460.
36. For reviews on rotaxanes and catenanes, see: a) C. O. Dietrich-Buchecker, J.-P. Sauvage, Chem. Rev. 1987, 87, 795-810 b) W. H. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843 c) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828 d)R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944 e) J.-P. Sauvage, C. Dietrich-Buchecker, Catenanes, Rotaxanes and Knots, Wiley-VCH. Weinheim, Germany, 1999;
37. For reviews on rotaxanes and catenanes, see: a) C. O. Dietrich-Buchecker, J.-P. Sauvage, Chem. Rev. 1987, 87, 795-810 b) W. H. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843 c) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828 d)R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944 e) J.-P. Sauvage, C. Dietrich-Buchecker, Catenanes, Rotaxanes and Knots, Wiley-VCH. Weinheim, Germany, 1999;
38. For reviews on rotaxanes and catenanes, see: a) C. O. Dietrich-Buchecker, J.-P. Sauvage, Chem. Rev. 1987, 87, 795-810 b) W. H. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843 c) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828 d)R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944 e) J.-P. Sauvage, C. Dietrich-Buchecker, Catenanes, Rotaxanes and Knots, Wiley-VCH. Weinheim, Germany, 1999;
39. For reviews on rotaxanes and catenanes, see: a) C. O. Dietrich-Buchecker, J.-P. Sauvage, Chem. Rev. 1987, 87, 795-810 b) W. H. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843 c) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828 d)R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944 e) J.-P. Sauvage, C. Dietrich-Buchecker, Catenanes, Rotaxanes and Knots, Wiley-VCH. Weinheim, Germany, 1999;
40. For reviews on rotaxanes and catenanes, see: a) C. O. Dietrich-Buchecker, J.-P. Sauvage, Chem. Rev. 1987, 87, 795-810 b) W. H. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843 c) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828 d)R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944 e) J.-P. Sauvage, C. Dietrich-Buchecker, Catenanes, Rotaxanes and Knots, Wiley-VCH. Weinheim, Germany, 1999;
41. For reviews on rotaxanes and catenanes, see: a) C. O. Dietrich-Buchecker, J.-P. Sauvage, Chem. Rev. 1987, 87, 795-810 b) W. H. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843 c) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828 d)R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944 e) J.-P. Sauvage, C. Dietrich-Buchecker, Catenanes, Rotaxanes and Knots, Wiley-VCH. Weinheim, Germany, 1999;
42. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
43. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
44. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
45. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
46. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
47. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
48. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
49. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
50. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
51. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
52. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
53. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
54. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
55. For the synthesis of amide linked rotaxanes, see f) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. Chem. 1995, 739-743 g) F. Vögtle, R. Jäger, M. Händel, S. Ottens-Hildebrandt, T. Schmidt, Synthesis 1996, 353-356 h) F. Vögtle, F. Ahuis, S. Baumann, J. L. Sessler, Liebigs Ann. Chem. 1996, 921-926 i) F. Vögtle, T. Dünnwald, M. Händel, R. Jäger, S. Meier, G. Harder, Chem. Eur. J. 1996, 2, 640-643 j) M. Händel, M. Plevoets, S. Gestermann, F. Vögtle, Angew. Chem. 1997, 109, 1248-1250; Angew. Chem. Int. Ed. Engt. 1997, 36, 1199-1201 k) G. A. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663 l)C. Heim, A. Affeid, M. Nieger, F. Vögtle, Helv. Chim. Acta 1999, 82, 1-14; For the synthesis of amide linked catenanes, see m) C. A. Hunter, J. Am. Chem. Soc. 1992, 104, 5303-5311 n) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622 o) Y. Geerts, D. Muscat, K. Müllen, Macromol. Chem. Phys. 1995, 196, 3425-3435 p) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. 1995, 107, 1324-1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216.
56. T. Dünnwald, R. Jäger, F. Vögtle, Chem. Eur. J. 1997, 3, 2043-2051.
57. R. Jäger, T. Schmidt, D. Karbach, F. Vögtle, Synlett 1996, 732-725.
58. In a [1]rotaxane the wheel and the axle of a [2]rotaxane are connected covalently. This could be formally regarded as one molecule in the classical sense, since the two parts are not only linked mechanically.
59. In a 〈n〉pretzelane the two mechanically bound macrocycles of a catenane are connected covalently. This leads to molecules with a topology of a pretzel, which we call "pretzelane".
60. C. Yamamoto, Y. Okamoto, T. Schmidt, R. Jäger, F. Vögtle, J. Am. Chem. Soc. 1997, 119, 10547-10548. We have been able to confirm the structure of both substances, 1 and 2, by X-ray structual analyses. New semi-empirical methods enabled us to calculate the CD-spectra based on the X-ray data and we are grateful to Dr. S. Grimme for cooperating in this matter.
61. 〈n〉 describes the number of methylene groups in the bridge of the pretzelane or the [1]rotaxane. This prefix was used by us formally in the field of 〈n〉phanes, 〈n〉beltanes and 〈n〉tubes to define the number of benzene and arene units; see: W. Boomgaarden, F. Vögtle. M. Nieger, H. Hupfer, Chem. Eur. J. 1999, 5, 345-355.
62. The mono- and dibromosulphonamide[2]rotaxancs which were formed as side products of the intramolecular cyclization reaction were analysed by FAB- or MALDI-TOF mass spectrometry and are not cited in the Experimental Section.
63. The [1]〈n〉rotaxane 4i and the [1]〈n〉rolaxane 4j were detected by FAB-MS, but a preparative isolation was not possible.
64. C. A. Hunter, M. J. Packer, Chem. Eur. J. 1999, 5, 1891-1897.
65. Chiralcel OD: cellulosetris[3,5(dimethylphenyl)cabamate]; E. Yashima, Y. Okamoto, Bull. Chem. Soc. Jpn. 1995, 68, 3289-3307. For a review, see: Y. Okamoto, E. Yashima, Angew. Chem. 1998, 110, 1072-1095; Angew. Chem. Int. Ed. 1998, 37, 1020-1043.
66. Chiralcel OD: cellulosetris[3,5(dimethylphenyl)cabamate]; E. Yashima, Y. Okamoto, Bull. Chem. Soc. Jpn. 1995, 68, 3289-3307. For a review, see: Y. Okamoto, E. Yashima, Angew. Chem. 1998, 110, 1072-1095; Angew. Chem. Int. Ed. 1998, 37, 1020-1043.
67. Chiralcel OD: cellulosetris[3,5(dimethylphenyl)cabamate]; E. Yashima, Y. Okamoto, Bull. Chem. Soc. Jpn. 1995, 68, 3289-3307. For a review, see: Y. Okamoto, E. Yashima, Angew. Chem. 1998, 110, 1072-1095; Angew. Chem. Int. Ed. 1998, 37, 1020-1043.
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70. R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413-447; Angew. Chem. Int. Ed. Engl. 1966, 5, 385-418; V. Prelog, G. Helmchen, Angew. Chem. 1982, 94, 614-631; Angew. Chem. Int. Ed. Engl. 1982, 21, 567-584.
71. R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413-447; Angew. Chem. Int. Ed. Engl. 1966, 5, 385-418; V. Prelog, G. Helmchen, Angew. Chem. 1982, 94, 614-631; Angew. Chem. Int. Ed. Engl. 1982, 21, 567-584.
72. R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413-447; Angew. Chem. Int. Ed. Engl. 1966, 5, 385-418; V. Prelog, G. Helmchen, Angew. Chem. 1982, 94, 614-631; Angew. Chem. Int. Ed. Engl. 1982, 21, 567-584.
73. R. Schmieder, G. M. Hübner, C. Seel, F. Vögtle, Angew. Chem. 1999, 111, 3741-3743;