Conformational studies of calix[5]arenes containing a single alkanediyl bridge

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 10, 1998, Pages 2261-2269

  Biali, Silvio E ^a   Böhmer, Volker ^b   Columbus, Ishay ^a   Ferguson, George ^c   Grüttner, Cordula ^b   Grynszpan, Flavio ^a   Paulus, Erich F ^d   Thondorf, Iris ^e  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

^c UNIVERSITY OF GUELPH   (Canada)

^d SANOFI   (France)

^e MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0141695644     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803470b     Document Type: Article

References (35)

1. For a review on calixarenes see: V. Böhmer, Angew. Chem., 1995, 107, 785; Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
2. For a review on calixarenes see: V. Böhmer, Angew. Chem., 1995, 107, 785; Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
3. Up to 20% are available by a one-pot reaction: D. R. Stewart and C. D. Gutsche, Org. Prep. Proc. Int., 1993, 25, 137; see also K. Iwamoto, K. Araki and S. Shinkai, Bull. Chem. Soc. Jpn., 1994, 67, 1499.
4. Up to 20% are available by a one-pot reaction: D. R. Stewart and C. D. Gutsche, Org. Prep. Proc. Int., 1993, 25, 137; see also K. Iwamoto, K. Araki and S. Shinkai, Bull. Chem. Soc. Jpn., 1994, 67, 1499.
5. For example, the number of partially O-alkylated derivatives, as well as the number of potential conformational isomers in a completely O-alkylated product is higher than with calix[4]arenes.
6. D. R. Stewart, M. Krawieck, R. P. Kashyap, W. H. Watson and C. D. Gutsche, J. Am. Chem. Soc., 1995, 117, 586.
7. For recent examples of guest binding in the cavity of calix[5]arene derivatives see: (a) T. Haino, M. Yanase and Y. Fukazawa, Tetrahedron Lett., 1997, 38, 3739; (b) T. Haino, M. Yanase and Y. Fukazawa, Angew. Chem., 1998, 110, 1004; Angew. Chem., Int. Ed. Engl. 1998, 37, 997; (c) S. Pappalardo and M. F. Parisi, J. Org. Chem., 1996, 61, 8724; (d) R. Arnecke, V. Böhmer, R. Cacciapaglia, A. Dalla Cort and L. Mandolini, Tetrahedron, 1997, 53, 4901; (e) F. Arnaud-Neu, S. Fuangswasdi, A. Notti, S. Pappalardo and M. F. Parisi, Angew. Chem., 1998, 110, 120; (f) see also J. W. Steed, C. P. Johnson, R. K. Juneja, R. S. Burkhalter and J. L. Atwood, Supramol. Chem., 1996, 6, 235.
8. For recent examples of guest binding in the cavity of calix[5]arene derivatives see: (a) T. Haino, M. Yanase and Y. Fukazawa, Tetrahedron Lett., 1997, 38, 3739; (b) T. Haino, M. Yanase and Y. Fukazawa, Angew. Chem., 1998, 110, 1004; Angew. Chem., Int. Ed. Engl. 1998, 37, 997; (c) S. Pappalardo and M. F. Parisi, J. Org. Chem., 1996, 61, 8724; (d) R. Arnecke, V. Böhmer, R. Cacciapaglia, A. Dalla Cort and L. Mandolini, Tetrahedron, 1997, 53, 4901; (e) F. Arnaud-Neu, S. Fuangswasdi, A. Notti, S. Pappalardo and M. F. Parisi, Angew. Chem., 1998, 110, 120; (f) see also J. W. Steed, C. P. Johnson, R. K. Juneja, R. S. Burkhalter and J. L. Atwood, Supramol. Chem., 1996, 6, 235.
9. For recent examples of guest binding in the cavity of calix[5]arene derivatives see: (a) T. Haino, M. Yanase and Y. Fukazawa, Tetrahedron Lett., 1997, 38, 3739; (b) T. Haino, M. Yanase and Y. Fukazawa, Angew. Chem., 1998, 110, 1004; Angew. Chem., Int. Ed. Engl. 1998, 37, 997; (c) S. Pappalardo and M. F. Parisi, J. Org. Chem., 1996, 61, 8724; (d) R. Arnecke, V. Böhmer, R. Cacciapaglia, A. Dalla Cort and L. Mandolini, Tetrahedron, 1997, 53, 4901; (e) F. Arnaud-Neu, S. Fuangswasdi, A. Notti, S. Pappalardo and M. F. Parisi, Angew. Chem., 1998, 110, 120; (f) see also J. W. Steed, C. P. Johnson, R. K. Juneja, R. S. Burkhalter and J. L. Atwood, Supramol. Chem., 1996, 6, 235.
10. For recent examples of guest binding in the cavity of calix[5]arene derivatives see: (a) T. Haino, M. Yanase and Y. Fukazawa, Tetrahedron Lett., 1997, 38, 3739; (b) T. Haino, M. Yanase and Y. Fukazawa, Angew. Chem., 1998, 110, 1004; Angew. Chem., Int. Ed. Engl. 1998, 37, 997; (c) S. Pappalardo and M. F. Parisi, J. Org. Chem., 1996, 61, 8724; (d) R. Arnecke, V. Böhmer, R. Cacciapaglia, A. Dalla Cort and L. Mandolini, Tetrahedron, 1997, 53, 4901; (e) F. Arnaud-Neu, S. Fuangswasdi, A. Notti, S. Pappalardo and M. F. Parisi, Angew. Chem., 1998, 110, 120; (f) see also J. W. Steed, C. P. Johnson, R. K. Juneja, R. S. Burkhalter and J. L. Atwood, Supramol. Chem., 1996, 6, 235.
11. For recent examples of guest binding in the cavity of calix[5]arene derivatives see: (a) T. Haino, M. Yanase and Y. Fukazawa, Tetrahedron Lett., 1997, 38, 3739; (b) T. Haino, M. Yanase and Y. Fukazawa, Angew. Chem., 1998, 110, 1004; Angew. Chem., Int. Ed. Engl. 1998, 37, 997; (c) S. Pappalardo and M. F. Parisi, J. Org. Chem., 1996, 61, 8724; (d) R. Arnecke, V. Böhmer, R. Cacciapaglia, A. Dalla Cort and L. Mandolini, Tetrahedron, 1997, 53, 4901; (e) F. Arnaud-Neu, S. Fuangswasdi, A. Notti, S. Pappalardo and M. F. Parisi, Angew. Chem., 1998, 110, 120; (f) see also J. W. Steed, C. P. Johnson, R. K. Juneja, R. S. Burkhalter and J. L. Atwood, Supramol. Chem., 1996, 6, 235.
12. For recent examples of guest binding in the cavity of calix[5]arene derivatives see: (a) T. Haino, M. Yanase and Y. Fukazawa, Tetrahedron Lett., 1997, 38, 3739; (b) T. Haino, M. Yanase and Y. Fukazawa, Angew. Chem., 1998, 110, 1004; Angew. Chem., Int. Ed. Engl. 1998, 37, 997; (c) S. Pappalardo and M. F. Parisi, J. Org. Chem., 1996, 61, 8724; (d) R. Arnecke, V. Böhmer, R. Cacciapaglia, A. Dalla Cort and L. Mandolini, Tetrahedron, 1997, 53, 4901; (e) F. Arnaud-Neu, S. Fuangswasdi, A. Notti, S. Pappalardo and M. F. Parisi, Angew. Chem., 1998, 110, 120; (f) see also J. W. Steed, C. P. Johnson, R. K. Juneja, R. S. Burkhalter and J. L. Atwood, Supramol. Chem., 1996, 6, 235.
13. For recent examples of guest binding in the cavity of calix[5]arene derivatives see: (a) T. Haino, M. Yanase and Y. Fukazawa, Tetrahedron Lett., 1997, 38, 3739; (b) T. Haino, M. Yanase and Y. Fukazawa, Angew. Chem., 1998, 110, 1004; Angew. Chem., Int. Ed. Engl. 1998, 37, 997; (c) S. Pappalardo and M. F. Parisi, J. Org. Chem., 1996, 61, 8724; (d) R. Arnecke, V. Böhmer, R. Cacciapaglia, A. Dalla Cort and L. Mandolini, Tetrahedron, 1997, 53, 4901; (e) F. Arnaud-Neu, S. Fuangswasdi, A. Notti, S. Pappalardo and M. F. Parisi, Angew. Chem., 1998, 110, 120; (f) see also J. W. Steed, C. P. Johnson, R. K. Juneja, R. S. Burkhalter and J. L. Atwood, Supramol. Chem., 1996, 6, 235.
14. See for instance: (a) J. F. Gallagher, G. Ferguson, V. Böhmer and D. Kraft, Acta Crystallogr., Sect. C, 1994, 50, 73; (b) M. Perrin and S. Lecocq, J. Inclusion Phenom. Mol. Recognit. Chem., 1991, 11, 171.
15. See for instance: (a) J. F. Gallagher, G. Ferguson, V. Böhmer and D. Kraft, Acta Crystallogr., Sect. C, 1994, 50, 73; (b) M. Perrin and S. Lecocq, J. Inclusion Phenom. Mol. Recognit. Chem., 1991, 11, 171.
16. (a) J. W. Steed, C. P. Johnson, C. L. Barnes, R. K. Juneja, J. L. Atwood, S. Reilly, R. L. Hollis, P. H. Smith and D. L. Clark, J. Am. Chem. Soc., 1996, 117, 11 426;
17. (b) C. P. Johnson, J. L. Atwood, J. W. Steed, C. B. Bauer and R. D. Rogers, Inorg. Chem., 1996, 35, 2602.
18. J. M. Van Gelder, O. Aleksiuk and S. E. Biali, J. Org. Chem., 1996, 61, 8419.
19. S. E. Biali, V. Böhmer, S. Cohen, G. Ferguson, C. Grüttner, F. Grynszpan, E. F. Paulus, I. Thondorf and W. Vogt, J. Am. Chem. Soc., 1996, 118, 12938.
20. G. Sartori, R. Maggi, F. Bigi, A. Arduini, A. Pastorio and C. Porta, J. Chem. Soc., Perkin Trans, 1, 1994, 1657.
21. M. Bergamaschi, F. Bigi, M. Lanfranchi, R. Maggi, A. Pastorio, M. A. Pellinghelli, F. Feri, C. Porta and G. Sartori, Tetrahedron. 1997, 53, 13 037.
22. K. No and K. M. Kwan, Synthesis, 1996, 1293.
23. Compare also T. Haino, T. Harano, K. Matsumura and Y. Fukazawa, Tetrahedron Lett., 1996, 36, 5793.
24. This downfield shift of the axial protons in the cone conformation of endo-calix[4]arenes is caused by the proximity to the OH groups, since in exo-calix[4]arenes the equatorial protons appear at lower field. See: S. E. Biali, V. Böhmer, J. Brenn, M. Frings, I. Thondorf, W. Vogt and J. Wöhnert, J. Org. Chem., 1997, 62, 8350.
25. F. A. L. Anet and V. J. Basus, J. Magn. Reson., 1978, 32, 339. For papers using this method see for example: S. P. Adams and H. W. Whitlock, J. Am. Chem. Soc., 1982, 104, 1602; D. Casarini, L. Lunazzi and D. Macciantelli, J. Chem. Soc., Perkin Trans. 2, 1985, 1839.
26. F. A. L. Anet and V. J. Basus, J. Magn. Reson., 1978, 32, 339. For papers using this method see for example: S. P. Adams and H. W. Whitlock, J. Am. Chem. Soc., 1982, 104, 1602; D. Casarini, L. Lunazzi and D. Macciantelli, J. Chem. Soc., Perkin Trans. 2, 1985, 1839.
27. F. A. L. Anet and V. J. Basus, J. Magn. Reson., 1978, 32, 339. For papers using this method see for example: S. P. Adams and H. W. Whitlock, J. Am. Chem. Soc., 1982, 104, 1602; D. Casarini, L. Lunazzi and D. Macciantelli, J. Chem. Soc., Perkin Trans. 2, 1985, 1839.
28. C. D. Gutsche and L. J. Bauer, J. Am. Chem. Soc., 1985, 107, 6052.
29. -1 was found for a "resorcinol derived" calix[5]arene consisting of five 2,4-dihydroxybenzophenone units: M. Tabatabai, W. Vogt, V. Böhmer, G. Ferguson and E. F. Paulus, Supramol. Chem., 1994, 4, 147.
30. This conformation can be designated as TTTtt(17.3), see I. Thondorf and J. Brenn, J. Chem. Soc., Perkin Trans. 2, 1997, 2293.
31. J. F. Gallagher, G. Ferguson, V. Böhmer and D. Kraft, Acta Crystallogr., Sect. C, 1994, 50, 73; and references cited there.
32. For a recent example with an average O⋯O-distance of 2.955 À see: L. Dumazet, N. Ehlinger, F. Vocanson, S. Lecocq, R. Lamartine and M. Perrin, J. Inclusion Phenom. Mol. Recognit. Chem., 1997, 29, 175.
33. I. Thondorf, G. Hillig, W. Brandt, J. Brenn, A. Barth and V. Böhmer, J. Chem. Soc., Perkin Trans. 2, 1994, 2259.
34. (a) J. Gasteiger and M. Marsili, Tetrahedron, 1980, 36, 3219;
35. (b) M. Marsili and J. Gasteiger, Croat. Chem. Acta, 1980, 53, 601.