Concave reagents 18: Synthesis, conformational behavior, and basicity of new pyridine-bridged calix[6]arenes

Liebigs Annales

Volumn , Issue 9, 1996, Pages 1367-1373

  Ross, Haymo ^a   Lüning, Ulrich ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

Calixarenes; Concave reagents; Pyridines

Indexed keywords

EID: 33749276943     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960905     Document Type: Article

References (36)

1. Part 17: U. Lüning, H. Baumgartner, C. Wangnick, Tetrahedron 1996, 52, 599-604.
2. U. Lüning, Top. Curr. Chem. 1995, 175, 57-99, and ref.
3. Diastercoselective protonations: U. Lüning, M. Müller, Angew. Chem. 1992, 104, 99-102;
4. Angew. Chem. Int. Ed. Engl. 1992, 31, 80-82.
5. Addition of alcohols to ketenes: U. Lüning, R. Baumstark, W. Schyja, Liebigs Ann. Chem. 1991, 999-1002.
6. Lewis acid catalyzed Diels-Alder reactions: M. Gelbert, Ph. D. Thesis, University of Freiburg, 1995.
7. H. Ross, U. Lüning, Angew. Chem. 1995, 107, 2723-2725;
8. Angew. Chem. Int. Ed. Engl. 1995, 34, 2555-2557.
9. C. D. Gutsche, Calixarenes, The Royal Society of Chemistry, Cambridge, 1989.
10. Calixarenes, a Versatile Class of Macrocyclic Compounds (Ed.: I. Vicens, V. Böhmer), Kluwer Academic Publishers, Dordrecht, 1991.
11. V. Böhmer, Angew. Chem. 1995, 107, 785-898;
12. Angew. Chem. Im. Ed. Engl. 1995, 34, 713-745.
13. C. D. Gutsche, B. Dhawan, M. Leonis, D. Stewart, Org. Synth. 1990, 68, 238-242.
14. N. Tokitoh, T. Saiki, R. Okazaki, J. Chem. Soc. Chem. Commun. 1995, 1899-1900.
15. D. Kraft, V. Böhmer, W. Vogt, G. Ferguson, J. F. Gallagher, J. Chem. Soc. Perkin Trans. 1, 1994, 1221-1230.
16. P. Neri, G. Ferguson, J. F. Gallagher, S. Pappalardo, Tetrahedron Lett. 1992, 33, 7403-7406.
17. S. Kanamathareddy, C. D. Gutsche, J. Am. Chem. Soc. 1993, 115, 6572-6579.
18. P. Neri, C. Rocco, G. M. L. Consoli, M. Piattelli, J. Org. Chem. 1993, 58, 6535-6537.
19. A,D-bridging is defined as the connection of two opposite phenol rings of a calix[6]arene. The alternative term 1,4-bridging does not correspond to the numbering of the calix[6]arene oxygene atoms (37-42).
20. A. Casnati, P. Jacopozzi, A. Pochini, F. Ugozzoli, R. Cacciapaglia, L. Mandolini, R. Ungaro, Tetrahedron 1995, 51, 591-598.
21. H. Otsuka, K. Araki, H. Matsumoto, T. Harada, S. Shinkai, J. Org. Chem. 1995, 60, 4862-4867.
22. H. Otsuka, K. Araki, S. Shinkai, J. Org. Chem. 1994, 59, 1542-1547.
23. L. Müller, J. Am. Chem. Soc. 1979, 101, 4481-4484.
24. J. S. Rogers, C. D. Gutsche, J. Org. Chem. 1992, 57, 3152-3159.
25. S. Kanamathareddy, C. D. Gutsche, J. Org. Chem. 1994, 59, 3871-3879.
26. This rule was first discovered in calix[4]arenes: C. Jaime, J. de Mendoza, P. Prados, P. M. Nieto, C. Sánchez. J. Org. Chem. 1991, 56, 3372-3376.
27. S. Pappalardo, L. Giunta, M. Foti, G. Ferguson, J. F. Gallagher, B. Kaitner, J. Org. Chem. 1992, 57, 2611-2624.
28. P. Neri, M. Foti, G. Ferguson, J. F. Gallagher, B. Kaitner, M. Pons, M. A. Molins, L. Giunta, S. Pappalardo, J. Am. Chem. Soc. 1992, 114, 7814-7821.
29. [19a] U. Lüning, M. Müller, Liebigs Ann. Chem. 1989, 367-374.
30. [19b] U. Lüning, R. Baumstark, K. Peters, H. G. v. Sehnering, Liebigs Ann. Chem. 1990, 129-143.
31. On predicted pK values of 2-picolinium ions: A. Fischer, M. J. King, F. P. Robinson, Can. J. Chem. 1978, 56, 3059-3067.
32. [21a] P. D. J. Grootenhuis, C. J. van Staveren, H. J. den Hertog, Jr., D. N. Reinhoudt, M. Bos, J. W. H. M. Uiterwijk, L. Kruise, S. Harkema, J. Chem. Soc. Chem. Commun. 1984, 1412-1413.
33. [21b] P. D. J. Grootenhuis, J. W. H. M. Uiterwijk, D. N. Reinhoudt, C. J. van Staveren, E. J. R. Sudhölter, M. Bos, J. van Eerden, W. T. Klooster, L. Kruise, S. Harkema, J. Am. Chem. Soc. 1986, 108, 780-788.
34. 3 of 1a see ref. 4.
35. W. Baker, K. M. Buggle, J. F W. McOmie, D. A. M. Watkins, J. Chem. Soc. 1958, 3594-3603.
36. E. Weber, F. Vögtle, H.-P. Josel, G. R. Newkome, W. E. Pucket, Chem. Ber. 1983, 116, 1906-1913.