Synthesis and properties of shape-persistent macrocyclic amphiphiles with switchable amphiphilic portions

Chemistry - A European Journal

Volumn 4, Issue 12, 1998, Pages 2423-2434

  Höger, Sigurd ^a   Meckenstock, Anne Désirée ^a   Müller, Sarah ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

Cyclizations; Macrocycles; Supramolecular chemistry

Indexed keywords

AMPHOPHILE; MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0031796182     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19981204)4:12<2423::AID-CHEM2423>3.0.CO;2-8     Document Type: Article

References (75)

1. Recent examples: a) M. R. Ghadiri, K. Kohayashi, J. R. Granja, R. K. Chadha, D. E. McRee, Angew. Chem. 1995, 107, 76; Angew. Chem. Int. Ed Engl. 1995, 34, 93; b) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 1615; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451; c) D. Venkataraman, S. Lee, J. Zhang, J. S Moore, Nature, 1994, 371, 591; d) S. Andersen, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596; e) H. L. Anderson, A. Bashall, K. Hendrick, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1994, 106, 445; Angew. Chem. Int. Ed. Engl. 1994, 33, 429, and references therein.
2. Recent examples: a) M. R. Ghadiri, K. Kohayashi, J. R. Granja, R. K. Chadha, D. E. McRee, Angew. Chem. 1995, 107, 76; Angew. Chem. Int. Ed Engl. 1995, 34, 93; b) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 1615; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451; c) D. Venkataraman, S. Lee, J. Zhang, J. S Moore, Nature, 1994, 371, 591; d) S. Andersen, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596; e) H. L. Anderson, A. Bashall, K. Hendrick, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1994, 106, 445; Angew. Chem. Int. Ed. Engl. 1994, 33, 429, and references therein.
3. Recent examples: a) M. R. Ghadiri, K. Kohayashi, J. R. Granja, R. K. Chadha, D. E. McRee, Angew. Chem. 1995, 107, 76; Angew. Chem. Int. Ed Engl. 1995, 34, 93; b) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 1615; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451; c) D. Venkataraman, S. Lee, J. Zhang, J. S Moore, Nature, 1994, 371, 591; d) S. Andersen, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596; e) H. L. Anderson, A. Bashall, K. Hendrick, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1994, 106, 445; Angew. Chem. Int. Ed. Engl. 1994, 33, 429, and references therein.
4. Recent examples: a) M. R. Ghadiri, K. Kohayashi, J. R. Granja, R. K. Chadha, D. E. McRee, Angew. Chem. 1995, 107, 76; Angew. Chem. Int. Ed Engl. 1995, 34, 93; b) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 1615; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451; c) D. Venkataraman, S. Lee, J. Zhang, J. S Moore, Nature, 1994, 371, 591; d) S. Andersen, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596; e) H. L. Anderson, A. Bashall, K. Hendrick, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1994, 106, 445; Angew. Chem. Int. Ed. Engl. 1994, 33, 429, and references therein.
5. Recent examples: a) M. R. Ghadiri, K. Kohayashi, J. R. Granja, R. K. Chadha, D. E. McRee, Angew. Chem. 1995, 107, 76; Angew. Chem. Int. Ed Engl. 1995, 34, 93; b) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 1615; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451; c) D. Venkataraman, S. Lee, J. Zhang, J. S Moore, Nature, 1994, 371, 591; d) S. Andersen, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596; e) H. L. Anderson, A. Bashall, K. Hendrick, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1994, 106, 445; Angew. Chem. Int. Ed. Engl. 1994, 33, 429, and references therein.
6. Recent examples: a) M. R. Ghadiri, K. Kohayashi, J. R. Granja, R. K. Chadha, D. E. McRee, Angew. Chem. 1995, 107, 76; Angew. Chem. Int. Ed Engl. 1995, 34, 93; b) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 1615; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451; c) D. Venkataraman, S. Lee, J. Zhang, J. S Moore, Nature, 1994, 371, 591; d) S. Andersen, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596; e) H. L. Anderson, A. Bashall, K. Hendrick, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1994, 106, 445; Angew. Chem. Int. Ed. Engl. 1994, 33, 429, and references therein.
7. Recent examples: a) M. R. Ghadiri, K. Kohayashi, J. R. Granja, R. K. Chadha, D. E. McRee, Angew. Chem. 1995, 107, 76; Angew. Chem. Int. Ed Engl. 1995, 34, 93; b) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 1615; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451; c) D. Venkataraman, S. Lee, J. Zhang, J. S Moore, Nature, 1994, 371, 591; d) S. Andersen, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596; e) H. L. Anderson, A. Bashall, K. Hendrick, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1994, 106, 445; Angew. Chem. Int. Ed. Engl. 1994, 33, 429, and references therein.
8. Recent examples: a) M. R. Ghadiri, K. Kohayashi, J. R. Granja, R. K. Chadha, D. E. McRee, Angew. Chem. 1995, 107, 76; Angew. Chem. Int. Ed Engl. 1995, 34, 93; b) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 1615; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451; c) D. Venkataraman, S. Lee, J. Zhang, J. S Moore, Nature, 1994, 371, 591; d) S. Andersen, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596; e) H. L. Anderson, A. Bashall, K. Hendrick, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1994, 106, 445; Angew. Chem. Int. Ed. Engl. 1994, 33, 429, and references therein.
9. Recent examples: a) M. R. Ghadiri, K. Kohayashi, J. R. Granja, R. K. Chadha, D. E. McRee, Angew. Chem. 1995, 107, 76; Angew. Chem. Int. Ed Engl. 1995, 34, 93; b) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 1615; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451; c) D. Venkataraman, S. Lee, J. Zhang, J. S Moore, Nature, 1994, 371, 591; d) S. Andersen, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596; e) H. L. Anderson, A. Bashall, K. Hendrick, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1994, 106, 445; Angew. Chem. Int. Ed. Engl. 1994, 33, 429, and references therein.
10. For example, see for a comparison: a) H. A. Staab, K. Neunhoeffer, Synthesis 1974, 424; b) J. S. Moore, J. Zhang, Angew. Chem. 1992, 104, 873; Angew. Chem. Int. Ed. Engl. 1992, 31, 292; c) H. Staab, F. Binning, Chem. Ber. 1967, 100, 293; d) V. Hensel, K. Lützow, J. Jakob, K. Gessler, W. Saenger, A.-D. Schlüter, Angew. Chem. 1997, 109, 2768; Angew. Chem. Int. Ed. Engl. 1997, 36, 2654.
11. For example, see for a comparison: a) H. A. Staab, K. Neunhoeffer, Synthesis 1974, 424; b) J. S. Moore, J. Zhang, Angew. Chem. 1992, 104, 873; Angew. Chem. Int. Ed. Engl. 1992, 31, 292; c) H. Staab, F. Binning, Chem. Ber. 1967, 100, 293; d) V. Hensel, K. Lützow, J. Jakob, K. Gessler, W. Saenger, A.-D. Schlüter, Angew. Chem. 1997, 109, 2768; Angew. Chem. Int. Ed. Engl. 1997, 36, 2654.
12. For example, see for a comparison: a) H. A. Staab, K. Neunhoeffer, Synthesis 1974, 424; b) J. S. Moore, J. Zhang, Angew. Chem. 1992, 104, 873; Angew. Chem. Int. Ed. Engl. 1992, 31, 292; c) H. Staab, F. Binning, Chem. Ber. 1967, 100, 293; d) V. Hensel, K. Lützow, J. Jakob, K. Gessler, W. Saenger, A.-D. Schlüter, Angew. Chem. 1997, 109, 2768; Angew. Chem. Int. Ed. Engl. 1997, 36, 2654.
13. For example, see for a comparison: a) H. A. Staab, K. Neunhoeffer, Synthesis 1974, 424; b) J. S. Moore, J. Zhang, Angew. Chem. 1992, 104, 873; Angew. Chem. Int. Ed. Engl. 1992, 31, 292; c) H. Staab, F. Binning, Chem. Ber. 1967, 100, 293; d) V. Hensel, K. Lützow, J. Jakob, K. Gessler, W. Saenger, A.-D. Schlüter, Angew. Chem. 1997, 109, 2768; Angew. Chem. Int. Ed. Engl. 1997, 36, 2654.
14. For example, see for a comparison: a) H. A. Staab, K. Neunhoeffer, Synthesis 1974, 424; b) J. S. Moore, J. Zhang, Angew. Chem. 1992, 104, 873; Angew. Chem. Int. Ed. Engl. 1992, 31, 292; c) H. Staab, F. Binning, Chem. Ber. 1967, 100, 293; d) V. Hensel, K. Lützow, J. Jakob, K. Gessler, W. Saenger, A.-D. Schlüter, Angew. Chem. 1997, 109, 2768; Angew. Chem. Int. Ed. Engl. 1997, 36, 2654.
15. For example, see for a comparison: a) H. A. Staab, K. Neunhoeffer, Synthesis 1974, 424; b) J. S. Moore, J. Zhang, Angew. Chem. 1992, 104, 873; Angew. Chem. Int. Ed. Engl. 1992, 31, 292; c) H. Staab, F. Binning, Chem. Ber. 1967, 100, 293; d) V. Hensel, K. Lützow, J. Jakob, K. Gessler, W. Saenger, A.-D. Schlüter, Angew. Chem. 1997, 109, 2768; Angew. Chem. Int. Ed. Engl. 1997, 36, 2654.
16. See, for example: a) J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995; b) B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1992; c) F. Vögtle, Supramolekulare Chemie, 2nd ed., Teubner, Stuttgart, 1992.
17. See, for example: a) J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995; b) B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1992; c) F. Vögtle, Supramolekulare Chemie, 2nd ed., Teubner, Stuttgart, 1992.
18. See, for example: a) J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995; b) B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1992; c) F. Vögtle, Supramolekulare Chemie, 2nd ed., Teubner, Stuttgart, 1992.
19. See, for example: a) J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vögtle, Comprehensive Supramolecular Chemistry, Vol. 3, Cyclodextrines (Ed.: F. Vögtle), Elsevier, 1996; b) J. Szejtli, Cyclodextrin Technology, Kluver Academic, Dordrecht, 1988; c) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; d) W. Saenger, Angew. Chem. 1980, 92, 343; Angew. Chem. Int. Ed. Engl. 1980, 19, 344.
20. See, for example: a) J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vögtle, Comprehensive Supramolecular Chemistry, Vol. 3, Cyclodextrines (Ed.: F. Vögtle), Elsevier, 1996; b) J. Szejtli, Cyclodextrin Technology, Kluver Academic, Dordrecht, 1988; c) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; d) W. Saenger, Angew. Chem. 1980, 92, 343; Angew. Chem. Int. Ed. Engl. 1980, 19, 344.
21. See, for example: a) J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vögtle, Comprehensive Supramolecular Chemistry, Vol. 3, Cyclodextrines (Ed.: F. Vögtle), Elsevier, 1996; b) J. Szejtli, Cyclodextrin Technology, Kluver Academic, Dordrecht, 1988; c) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; d) W. Saenger, Angew. Chem. 1980, 92, 343; Angew. Chem. Int. Ed. Engl. 1980, 19, 344.
22. See, for example: a) J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vögtle, Comprehensive Supramolecular Chemistry, Vol. 3, Cyclodextrines (Ed.: F. Vögtle), Elsevier, 1996; b) J. Szejtli, Cyclodextrin Technology, Kluver Academic, Dordrecht, 1988; c) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; d) W. Saenger, Angew. Chem. 1980, 92, 343; Angew. Chem. Int. Ed. Engl. 1980, 19, 344.
23. See, for example: a) J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vögtle, Comprehensive Supramolecular Chemistry, Vol. 3, Cyclodextrines (Ed.: F. Vögtle), Elsevier, 1996; b) J. Szejtli, Cyclodextrin Technology, Kluver Academic, Dordrecht, 1988; c) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; d) W. Saenger, Angew. Chem. 1980, 92, 343; Angew. Chem. Int. Ed. Engl. 1980, 19, 344.
24. See, for example: a) J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vögtle, Comprehensive Supramolecular Chemistry, Vol. 3, Cyclodextrines (Ed.: F. Vögtle), Elsevier, 1996; b) J. Szejtli, Cyclodextrin Technology, Kluver Academic, Dordrecht, 1988; c) G. Wenz, Angew. Chem. 1994, 106, 851; Angew. Chem. Int. Ed. Engl. 1994, 33, 803; d) W. Saenger, Angew. Chem. 1980, 92, 343; Angew. Chem. Int. Ed. Engl. 1980, 19, 344.
25. a) S. Höger, V. Enkelmann, Angew. Chem. 1995, 107, 2917; Angew. Chem. Int. Ed. Engl. 1995, 34, 2713;
26. a) S. Höger, V. Enkelmann, Angew. Chem. 1995, 107, 2917; Angew. Chem. Int. Ed. Engl. 1995, 34, 2713;
27. b) S. Höger, S. Müller, L. Karcher, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1997, 38, 72.
28. C. J. Walter, H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1993, 458.
29. For reviews, see: a) A. D. Hamilton, in Bioorganic Chemistry Frontiers, Vol. 2 (Ed.: H. Dugas), Springer, Berlin-Heidelberg, 1991, pp. 115-174; b) D. E. Koshland, Angew. Chem. 1994, 106, 2468; Angew. Chem. Int. Ed. Engl, 1994, 33, 2375.
30. For reviews, see: a) A. D. Hamilton, in Bioorganic Chemistry Frontiers, Vol. 2 (Ed.: H. Dugas), Springer, Berlin-Heidelberg, 1991, pp. 115-174; b) D. E. Koshland, Angew. Chem. 1994, 106, 2468; Angew. Chem. Int. Ed. Engl, 1994, 33, 2375.
31. For reviews, see: a) A. D. Hamilton, in Bioorganic Chemistry Frontiers, Vol. 2 (Ed.: H. Dugas), Springer, Berlin-Heidelberg, 1991, pp. 115-174; b) D. E. Koshland, Angew. Chem. 1994, 106, 2468; Angew. Chem. Int. Ed. Engl, 1994, 33, 2375.
32. On the other hand, it has been suggested that in some cases the slight flexibility of host molecules, and their ability to undergo minor conformational changes to accomodate the guest, might be superior to an excessively rigid structure: R. E. Sheridan, H. W. Whitlock, Jr., J. Am. Chem. Soc. 1988, 110, 4071.
33. K. Okuyama, T. Hasegawa, M. Ito, N. Mikami, J. Phys. Chem. 1984, 88, 1711.
34. For other macrocyclic structures based on the phenyl-ethynyl backbone see also: a) F. Diederich, Nature 1994, 369, 199; b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 482; Angew. Chem. Int. Ed. Engl. 1994, 33, 486; c) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl 1994, 33, 869; d) A. de Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M. J. Cooney, L. T. Scott, Chem. Eur. J. 1995, 1, 124; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs J. Chem. Soc. Chem. Commun. 1994, 1257; f) R. Bürli, A. Vasella, Angew. Chem. 1997, 109, 1945; Angew. Chem. Int. Ed. Engl. 1997, 36, 1852; g) R. Bürli, A. Vasella, Helv. Chim. Acta, 1997, 80, 1027.
35. For other macrocyclic structures based on the phenyl-ethynyl backbone see also: a) F. Diederich, Nature 1994, 369, 199; b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 482; Angew. Chem. Int. Ed. Engl. 1994, 33, 486; c) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl 1994, 33, 869; d) A. de Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M. J. Cooney, L. T. Scott, Chem. Eur. J. 1995, 1, 124; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs J. Chem. Soc. Chem. Commun. 1994, 1257; f) R. Bürli, A. Vasella, Angew. Chem. 1997, 109, 1945; Angew. Chem. Int. Ed. Engl. 1997, 36, 1852; g) R. Bürli, A. Vasella, Helv. Chim. Acta, 1997, 80, 1027.
36. For other macrocyclic structures based on the phenyl-ethynyl backbone see also: a) F. Diederich, Nature 1994, 369, 199; b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 482; Angew. Chem. Int. Ed. Engl. 1994, 33, 486; c) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl 1994, 33, 869; d) A. de Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M. J. Cooney, L. T. Scott, Chem. Eur. J. 1995, 1, 124; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs J. Chem. Soc. Chem. Commun. 1994, 1257; f) R. Bürli, A. Vasella, Angew. Chem. 1997, 109, 1945; Angew. Chem. Int. Ed. Engl. 1997, 36, 1852; g) R. Bürli, A. Vasella, Helv. Chim. Acta, 1997, 80, 1027.
37. For other macrocyclic structures based on the phenyl-ethynyl backbone see also: a) F. Diederich, Nature 1994, 369, 199; b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 482; Angew. Chem. Int. Ed. Engl. 1994, 33, 486; c) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl 1994, 33, 869; d) A. de Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M. J. Cooney, L. T. Scott, Chem. Eur. J. 1995, 1, 124; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs J. Chem. Soc. Chem. Commun. 1994, 1257; f) R. Bürli, A. Vasella, Angew. Chem. 1997, 109, 1945; Angew. Chem. Int. Ed. Engl. 1997, 36, 1852; g) R. Bürli, A. Vasella, Helv. Chim. Acta, 1997, 80, 1027.
38. For other macrocyclic structures based on the phenyl-ethynyl backbone see also: a) F. Diederich, Nature 1994, 369, 199; b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 482; Angew. Chem. Int. Ed. Engl. 1994, 33, 486; c) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl 1994, 33, 869; d) A. de Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M. J. Cooney, L. T. Scott, Chem. Eur. J. 1995, 1, 124; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs J. Chem. Soc. Chem. Commun. 1994, 1257; f) R. Bürli, A. Vasella, Angew. Chem. 1997, 109, 1945; Angew. Chem. Int. Ed. Engl. 1997, 36, 1852; g) R. Bürli, A. Vasella, Helv. Chim. Acta, 1997, 80, 1027.
39. For other macrocyclic structures based on the phenyl-ethynyl backbone see also: a) F. Diederich, Nature 1994, 369, 199; b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 482; Angew. Chem. Int. Ed. Engl. 1994, 33, 486; c) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl 1994, 33, 869; d) A. de Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M. J. Cooney, L. T. Scott, Chem. Eur. J. 1995, 1, 124; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs J. Chem. Soc. Chem. Commun. 1994, 1257; f) R. Bürli, A. Vasella, Angew. Chem. 1997, 109, 1945; Angew. Chem. Int. Ed. Engl. 1997, 36, 1852; g) R. Bürli, A. Vasella, Helv. Chim. Acta, 1997, 80, 1027.
40. For other macrocyclic structures based on the phenyl-ethynyl backbone see also: a) F. Diederich, Nature 1994, 369, 199; b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 482; Angew. Chem. Int. Ed. Engl. 1994, 33, 486; c) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl 1994, 33, 869; d) A. de Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M. J. Cooney, L. T. Scott, Chem. Eur. J. 1995, 1, 124; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs J. Chem. Soc. Chem. Commun. 1994, 1257; f) R. Bürli, A. Vasella, Angew. Chem. 1997, 109, 1945; Angew. Chem. Int. Ed. Engl. 1997, 36, 1852; g) R. Bürli, A. Vasella, Helv. Chim. Acta, 1997, 80, 1027.
41. For other macrocyclic structures based on the phenyl-ethynyl backbone see also: a) F. Diederich, Nature 1994, 369, 199; b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 482; Angew. Chem. Int. Ed. Engl. 1994, 33, 486; c) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl 1994, 33, 869; d) A. de Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M. J. Cooney, L. T. Scott, Chem. Eur. J. 1995, 1, 124; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs J. Chem. Soc. Chem. Commun. 1994, 1257; f) R. Bürli, A. Vasella, Angew. Chem. 1997, 109, 1945; Angew. Chem. Int. Ed. Engl. 1997, 36, 1852; g) R. Bürli, A. Vasella, Helv. Chim. Acta, 1997, 80, 1027.
42. For other macrocyclic structures based on the phenyl-ethynyl backbone see also: a) F. Diederich, Nature 1994, 369, 199; b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 482; Angew. Chem. Int. Ed. Engl. 1994, 33, 486; c) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl 1994, 33, 869; d) A. de Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M. J. Cooney, L. T. Scott, Chem. Eur. J. 1995, 1, 124; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs J. Chem. Soc. Chem. Commun. 1994, 1257; f) R. Bürli, A. Vasella, Angew. Chem. 1997, 109, 1945; Angew. Chem. Int. Ed. Engl. 1997, 36, 1852; g) R. Bürli, A. Vasella, Helv. Chim. Acta, 1997, 80, 1027.
43. For other macrocyclic structures based on the phenyl-ethynyl backbone see also: a) F. Diederich, Nature 1994, 369, 199; b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 482; Angew. Chem. Int. Ed. Engl. 1994, 33, 486; c) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl 1994, 33, 869; d) A. de Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M. J. Cooney, L. T. Scott, Chem. Eur. J. 1995, 1, 124; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs J. Chem. Soc. Chem. Commun. 1994, 1257; f) R. Bürli, A. Vasella, Angew. Chem. 1997, 109, 1945; Angew. Chem. Int. Ed. Engl. 1997, 36, 1852; g) R. Bürli, A. Vasella, Helv. Chim. Acta, 1997, 80, 1027.
44. D. L. Morrison, S. Höger, Chem. Commun, 1996, 2313.
45. S. Höger, L. Karcher, unpublished results.
46. M. Brake, V. Enkelmann, U. H. F. Bunz, J. Org. Chem. 1996, 61, 1190.
47. V. Hensel, K. Lützow, A.-D. Schlüter, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1995, 36, 574.
48. f values. Moreover, a seperation of the two regio isomers was impossible by this method.
49. a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 4467;
50. b) Y. Tohda, K. Sonogashira, N. Hagihara, Synthesis 1977, 777.
51. See, for example also: a) P. Fitton, A. E. Rick, J. Organomet. Chem. 1971, 28, 287; b) R. Diercks, K. P. C. Vollhardt, Angew. Chem. 1986, 95, 268; Angew. Chem. Int. Ed. Engl. 1986, 25, 266; c) M. B. Goldfinger, T. M. Swager, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1994, 35, 274; d) J. D. Bradshaw, L. Guo, C. A. Tessier, W. G. Youngs, Organometallics 1996, 15, 2582.
52. See, for example also: a) P. Fitton, A. E. Rick, J. Organomet. Chem. 1971, 28, 287; b) R. Diercks, K. P. C. Vollhardt, Angew. Chem. 1986, 95, 268; Angew. Chem. Int. Ed. Engl. 1986, 25, 266; c) M. B. Goldfinger, T. M. Swager, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1994, 35, 274; d) J. D. Bradshaw, L. Guo, C. A. Tessier, W. G. Youngs, Organometallics 1996, 15, 2582.
53. See, for example also: a) P. Fitton, A. E. Rick, J. Organomet. Chem. 1971, 28, 287; b) R. Diercks, K. P. C. Vollhardt, Angew. Chem. 1986, 95, 268; Angew. Chem. Int. Ed. Engl. 1986, 25, 266; c) M. B. Goldfinger, T. M. Swager, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1994, 35, 274; d) J. D. Bradshaw, L. Guo, C. A. Tessier, W. G. Youngs, Organometallics 1996, 15, 2582.
54. See, for example also: a) P. Fitton, A. E. Rick, J. Organomet. Chem. 1971, 28, 287; b) R. Diercks, K. P. C. Vollhardt, Angew. Chem. 1986, 95, 268; Angew. Chem. Int. Ed. Engl. 1986, 25, 266; c) M. B. Goldfinger, T. M. Swager, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1994, 35, 274; d) J. D. Bradshaw, L. Guo, C. A. Tessier, W. G. Youngs, Organometallics 1996, 15, 2582.
55. See, for example also: a) P. Fitton, A. E. Rick, J. Organomet. Chem. 1971, 28, 287; b) R. Diercks, K. P. C. Vollhardt, Angew. Chem. 1986, 95, 268; Angew. Chem. Int. Ed. Engl. 1986, 25, 266; c) M. B. Goldfinger, T. M. Swager, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1994, 35, 274; d) J. D. Bradshaw, L. Guo, C. A. Tessier, W. G. Youngs, Organometallics 1996, 15, 2582.
56. a) A. M. Boldi, J. Anthony, C. B. Knobler, F. Diederich, Angew. Chem. 1992, 104, 1270; Angew. Chem. Int. Ed. Engl. 1992, 31, 1240;
57. a) A. M. Boldi, J. Anthony, C. B. Knobler, F. Diederich, Angew. Chem. 1992, 104, 1270; Angew. Chem. Int. Ed. Engl. 1992, 31, 1240;
58. b) O. Lavastre, L. Ollivier, P. H. Dixneuf, S. Sibandhit, Tetrahedron 1996, 52, 5495.
59. P. Liess, V. Hensel, A.-D. Schlüter, Liebigs Ann. 1996, 1037.
60. S. Höger, Liebigs Ann./Recueil 1997, 273.
61. A similar approach, the stepwise Pd-catalyzed coupling of (2)-1,2-dichloroethene with two different alkynes in order to prepare a monoprotected endiyne system, has also been reported: Y.-F. Lu, C. W. Harwig, A. G. Fallis, J. Org. Chem. 1993, 58, 4202.
62. H. L. Wheeeler, L. M. Liddle, Am. Chem. J. 1909, 42, 441.
63. a) F. B. McAllister, J. Kenner, J. Chem. Soc. 1928, 1914;
64. b) It is easier to prepare 3-bromo-5-iodo toluene from 4-methyl aniline as described for the synthesis of 3-bromo-5-iodo-tert-butyl benzene: S. Höger, A.-D- Meckenstock, H. Pellen, J. Org. Chem. 1997, 62, 4556.
65. For the use of piperidine in Hagihara coupling reactions see: M. Alami, F. Ferri, G. Linstrumelle, Tetrahedron Lett. 1993, 34, 6403.
66. We observed that kinked compounds like 5, 6 etc. show a higher tendency to tail than linear compounds like 19, 20 etc. when column Chromatographic purifications in multigram quantities were performed.
67. a) D. O'Krongly, S. R. Denmade, M. Y. Chiang, R. Breslow, J. Am. Chem. Soc. 1985, 107, 5544;
68. b) K. Kadei, F. Vögtle, Chem. Ber. 1991, 124, 909.
69. We were yet not able to isolate any material which indicates the formation of catenanes.
70. Macrocycles with analogous behavior have been also described by others, for example: a) J. S. Moore, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1993, 34, 170; b) A. de Meijere, F. Jaeckel, A. Simon, H. Borrmann, J. Köhler, D. Johnels, L. T. Scott, J. Am. Chem. Soc. 1991, 113, 3935.
71. Macrocycles with analogous behavior have been also described by others, for example: a) J. S. Moore, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1993, 34, 170; b) A. de Meijere, F. Jaeckel, A. Simon, H. Borrmann, J. Köhler, D. Johnels, L. T. Scott, J. Am. Chem. Soc. 1991, 113, 3935.
72. The aggregation of macrocyclic amphiphiles in the gas phase has been reported previously: S. Höger, J. Spickermann, D. L. Morrison, P. Dziezok, H. J. Räder, Macromolecules 1997, 30, 3110. However, the question whether this is a physical or chemical association is still under investigation.
73. For reports about the aggregation of phenyl - ethynyl based macrocycles see, for example: a) M. Kahr, Z. Xu, K. L. Walker, C. L. Wilkins, J. S. Moore, J. Am. Chem. Soc. 1994, 116, 4537; b) Y. Tobe, N. Utsumi, K. Kawabata, K. Naemura, Tetrahedron Lett. 1996, 37, 9325.
74. For reports about the aggregation of phenyl - ethynyl based macrocycles see, for example: a) M. Kahr, Z. Xu, K. L. Walker, C. L. Wilkins, J. S. Moore, J. Am. Chem. Soc. 1994, 116, 4537; b) Y. Tobe, N. Utsumi, K. Kawabata, K. Naemura, Tetrahedron Lett. 1996, 37, 9325.
75. The sensitivity of these protons towards the hydrogen bonding acceptor strength of the environment has also been used to investigate the interaction of the macrocycles with specific guest molecules (for example, ref [11]).