High-yield synthesis of ester, carbonate, and acetal rotaxanes by anion template assistance and their hydrolyric dethreading

Chemistry - A European Journal

Volumn 5, Issue 9, 1999, Pages 2692-2697

  Reuter, Carin ^a   Wienand, Wolfgang ^a   Hübner, Gosia M ^a   Seel, Christian ^a   Vögtle, Fritz ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Macrocycles; Molecular recognition; Supramolecular chemistry; Template effect; Wheeled reagents

Indexed keywords

ACETAL; CARBONIC ACID; CATENANE; DICHLOROMETHANE; ESTER; ROTAXANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032821870     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990903)5:9<2692::AID-CHEM2692>3.0.CO;2-F     Document Type: Article

References (53)

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11. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
12. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
13. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
14. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
15. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
16. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
17. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
18. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
19. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
20. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
21. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
22. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
23. e) Molecular Catenanes, Rotaxanes, and Knots (Ed. J. P. Sauvage, C. Dietrich-Buchecker). Wiley-VCH, Weinheim, 1999. Recent reports: M. Born, H. Ritter, Adv. Mater. 1996, 8, 149-151; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg, S. J. Teat, Chem. Commun. 1997, 897-898; A. Harada, J. Li, M. Kamachi, Chem. Commun. 1997, 1413-1414; W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36. 2511-2514; C. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438; M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612; D. A. Leigh, A. Murphy, J. P. Smart, M. S. Deleuze, F. Zerbetto, J. Am. Chem. Soc. 1998, 120, 6458-6467; N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P Sauvage, Chem. Eur. J. 1998, 4, 406-416; P. R. Ashton, M. C. T. Fyfe, M.-V. Martinez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534; T. Dünnwald, A. H. Parham, F. Vögtle, Synthesis 1998, 3, 339-348.
24. C. Wu, P. R. Lecvalier, Y. X. Shen, H. W. Gibson, Chem. Mat. 1991, 3, 569-572: F. Vögtle, M. Handel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; A. G. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663; S. Anderson, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 1997, 109, 1367-1370; Angew. Chem. Int. Ed. Engl. 1997, 36, 1310-1313.
25. C. Wu, P. R. Lecvalier, Y. X. Shen, H. W. Gibson, Chem. Mat. 1991, 3, 569-572: F. Vögtle, M. Handel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; A. G. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663; S. Anderson, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 1997, 109, 1367-1370; Angew. Chem. Int. Ed. Engl. 1997, 36, 1310-1313.
26. C. Wu, P. R. Lecvalier, Y. X. Shen, H. W. Gibson, Chem. Mat. 1991, 3, 569-572: F. Vögtle, M. Handel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; A. G. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663; S. Anderson, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 1997, 109, 1367-1370; Angew. Chem. Int. Ed. Engl. 1997, 36, 1310-1313.
27. C. Wu, P. R. Lecvalier, Y. X. Shen, H. W. Gibson, Chem. Mat. 1991, 3, 569-572: F. Vögtle, M. Handel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; A. G. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663; S. Anderson, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 1997, 109, 1367-1370; Angew. Chem. Int. Ed. Engl. 1997, 36, 1310-1313.
28. C. Wu, P. R. Lecvalier, Y. X. Shen, H. W. Gibson, Chem. Mat. 1991, 3, 569-572: F. Vögtle, M. Handel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; A. G. Johnston, D. A. Leigh, A. Murphy, J. P. Smart, M. D. Deegan, J. Am. Chem. Soc. 1996, 118, 10662-10663; S. Anderson, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 1997, 109, 1367-1370; Angew. Chem. Int. Ed. Engl. 1997, 36, 1310-1313.
29. G. M. Hübner, J. Gläser, C. Seel, F. Vögtle, Angew. Chem. 1999, 111, 395-398; Angew. Chem. Int. Ed. 1999, 38, 383-386.
30. G. M. Hübner, J. Gläser, C. Seel, F. Vögtle, Angew. Chem. 1999, 111, 395-398; Angew. Chem. Int. Ed. 1999, 38, 383-386.
31. Synthesis of the tetralactam macrocycle 2: C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311; F. J. Carver, C. A. Hunter, R. J. Shannon, J. Chem. Soc. Chem. Commun. 1994, 1277-1280; F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619.
32. Synthesis of the tetralactam macrocycle 2: C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311; F. J. Carver, C. A. Hunter, R. J. Shannon, J. Chem. Soc. Chem. Commun. 1994, 1277-1280; F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619.
33. Synthesis of the tetralactam macrocycle 2: C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311; F. J. Carver, C. A. Hunter, R. J. Shannon, J. Chem. Soc. Chem. Commun. 1994, 1277-1280; F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619.
34. Synthesis of the tetralactam macrocycle 2: C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311; F. J. Carver, C. A. Hunter, R. J. Shannon, J. Chem. Soc. Chem. Commun. 1994, 1277-1280; F. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628-1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619.
35. 1H NMR peak of the NH protons of the tetralactam host 2. The values are shifted by 1.7 to 1.8 ppm (cf. [4]).
36. S. Ottens-Hildebrandt, S. Meier, M. Nieger, F. Vögtle, E. Weber, Supramol. Chem. 1995, 5, 133-138; F. Vögtle, T. Dünnwald, T. Schmidt, Acc. Chem. Res. 1996, 29, 451-460; S. Braschohs, Thesis, University of Bonn, 1998. In catenanes derived from these lactams one amide group of each ring is inverted with the carbonyl pointing inwards to provide additional hydrogen bonds: S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; H. Adams, F. J. Carver, C. A. Hunter, J. Chem. Soc. Chem. Commun. 1995, 809-810. A rotaxane with one amide bond, which also appeared to be inverted, was reported: D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin. Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 752-756.
37. S. Ottens-Hildebrandt, S. Meier, M. Nieger, F. Vögtle, E. Weber, Supramol. Chem. 1995, 5, 133-138; F. Vögtle, T. Dünnwald, T. Schmidt, Acc. Chem. Res. 1996, 29, 451-460; S. Braschohs, Thesis, University of Bonn, 1998. In catenanes derived from these lactams one amide group of each ring is inverted with the carbonyl pointing inwards to provide additional hydrogen bonds: S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; H. Adams, F. J. Carver, C. A. Hunter, J. Chem. Soc. Chem. Commun. 1995, 809-810. A rotaxane with one amide bond, which also appeared to be inverted, was reported: D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin. Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 752-756.
38. S. Ottens-Hildebrandt, S. Meier, M. Nieger, F. Vögtle, E. Weber, Supramol. Chem. 1995, 5, 133-138; F. Vögtle, T. Dünnwald, T. Schmidt, Acc. Chem. Res. 1996, 29, 451-460; S. Braschohs, Thesis, University of Bonn, 1998. In catenanes derived from these lactams one amide group of each ring is inverted with the carbonyl pointing inwards to provide additional hydrogen bonds: S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; H. Adams, F. J. Carver, C. A. Hunter, J. Chem. Soc. Chem. Commun. 1995, 809-810. A rotaxane with one amide bond, which also appeared to be inverted, was reported: D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin. Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 752-756.
39. S. Ottens-Hildebrandt, S. Meier, M. Nieger, F. Vögtle, E. Weber, Supramol. Chem. 1995, 5, 133-138; F. Vögtle, T. Dünnwald, T. Schmidt, Acc. Chem. Res. 1996, 29, 451-460; S. Braschohs, Thesis, University of Bonn, 1998. In catenanes derived from these lactams one amide group of each ring is inverted with the carbonyl pointing inwards to provide additional hydrogen bonds: S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; H. Adams, F. J. Carver, C. A. Hunter, J. Chem. Soc. Chem. Commun. 1995, 809-810. A rotaxane with one amide bond, which also appeared to be inverted, was reported: D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin. Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 752-756.
40. S. Ottens-Hildebrandt, S. Meier, M. Nieger, F. Vögtle, E. Weber, Supramol. Chem. 1995, 5, 133-138; F. Vögtle, T. Dünnwald, T. Schmidt, Acc. Chem. Res. 1996, 29, 451-460; S. Braschohs, Thesis, University of Bonn, 1998. In catenanes derived from these lactams one amide group of each ring is inverted with the carbonyl pointing inwards to provide additional hydrogen bonds: S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; H. Adams, F. J. Carver, C. A. Hunter, J. Chem. Soc. Chem. Commun. 1995, 809-810. A rotaxane with one amide bond, which also appeared to be inverted, was reported: D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin. Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 752-756.
41. S. Ottens-Hildebrandt, S. Meier, M. Nieger, F. Vögtle, E. Weber, Supramol. Chem. 1995, 5, 133-138; F. Vögtle, T. Dünnwald, T. Schmidt, Acc. Chem. Res. 1996, 29, 451-460; S. Braschohs, Thesis, University of Bonn, 1998. In catenanes derived from these lactams one amide group of each ring is inverted with the carbonyl pointing inwards to provide additional hydrogen bonds: S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; H. Adams, F. J. Carver, C. A. Hunter, J. Chem. Soc. Chem. Commun. 1995, 809-810. A rotaxane with one amide bond, which also appeared to be inverted, was reported: D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin. Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 752-756.
42. S. Ottens-Hildebrandt, S. Meier, M. Nieger, F. Vögtle, E. Weber, Supramol. Chem. 1995, 5, 133-138; F. Vögtle, T. Dünnwald, T. Schmidt, Acc. Chem. Res. 1996, 29, 451-460; S. Braschohs, Thesis, University of Bonn, 1998. In catenanes derived from these lactams one amide group of each ring is inverted with the carbonyl pointing inwards to provide additional hydrogen bonds: S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; H. Adams, F. J. Carver, C. A. Hunter, J. Chem. Soc. Chem. Commun. 1995, 809-810. A rotaxane with one amide bond, which also appeared to be inverted, was reported: D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin. Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 752-756.
43. The carboxylate routes were hitherto not successful, therefore we did not consider these experiments here.
44. The following citations contain different rotaxane syntheses using, in each case, homologous, and therefore, axle precursors of different lengths: a) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822;
45. The following citations contain different rotaxane syntheses using, in each case, homologous, and therefore, axle precursors of different lengths: a) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822;
46. b) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-200;
47. b) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-200;
48. c) R. Isnin, A. E. Kaifer, J. Am. Chem. Soc. 1991, 113, 8188-8190; R. Isnin, A. E. Kaifer, Pure Appl. Chem. 1993, 65, 495-498;
49. c) R. Isnin, A. E. Kaifer, J. Am. Chem. Soc. 1991, 113, 8188-8190; R. Isnin, A. E. Kaifer, Pure Appl. Chem. 1993, 65, 495-498;
50. d) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; R. S. Wylie, D. H. Macartney, Supramol. Chem. 1993, 3, 29; D. H. Macartney, C. A. Waddling, Inorg. Chem. 1994, 33, 5912-5919.
51. d) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; R. S. Wylie, D. H. Macartney, Supramol. Chem. 1993, 3, 29; D. H. Macartney, C. A. Waddling, Inorg. Chem. 1994, 33, 5912-5919.
52. d) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; R. S. Wylie, D. H. Macartney, Supramol. Chem. 1993, 3, 29; D. H. Macartney, C. A. Waddling, Inorg. Chem. 1994, 33, 5912-5919.
53. Since the submission of this paper the new method has been successfully applied to the syntheses of rotaxanes with thioether and thioester axles.