Synthesis, structural characterization, and alkali-metal complexation of the six possible (1,3)- and (1,2)-bridged p-tert-butylcalix[4]crown-5 conformers bearing α-picolyl pendant groups

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 7770-7779

  Arnaud Neu, Francoise ^a,d   Ferguson, George ^b   Fuangswasdi, Saowarux ^c   Notti, Anna ^a   Pappalardo, Sebastiano ^a   Parisi, Melchiorre F ^b   Petringa, Ada ^c  

^a CNRS   (France)

^b UNIVERSITY OF GUELPH   (Canada)

^c UNIVERSITY OF MESSINA   (Italy)

^d UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3242766320     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980845h     Document Type: Article

References (53)

1. (a) Gutsche, C. D. In Calixarenes; Stoddart, J. F., Ed.; Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, U.K., 1989; Vol. 1.
2. (b) Calixarenes, a Versatile Class of Macrocydic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands, 1991.
3. Alfieri, C.; Dradi, E.; Pochini, A.; Ungaro, R.; Andreetti, G. D. J. Chem. Soc., Chem. Commun. 1983, 1075.
4. For a short review on calixcrown, see: Asfari, Z.; Wenger, S.; Vicens, J. J. Ind. Phenom. Mol. Recogn. 1994, 19, 137.
5. Pure Appl. Chem. 1995, 67, 1037.
6. (a) Kraft, D.; Arnecke, R.; Böhmer, V.; Vogt, W. Tetrahedron 1993,49,6019.
7. (b) Arnecke, R.; Böhmer, V.; Ferguson, G.; Pappalardo, S. Tetrahedron Lett. 1996, 37, 1497.
8. Arnaud-Neu, F.; Arnecke, R.; Böhmer, V.; Fanni, S.; Gordon, J. L. M.; Schwing-Weill, M.-J.; Vogt, W. J. Chem. Soc., Perkin Trans. 2 1996, 1855.
9. Pappalardo, S.; Parisi, M. F. J. Org. Chem. 1996, 61, 8724.
10. Casnati, A.; lacopozzi, P.; Pochini, A.; Ugozzoli, F.; Cacciapaglia, R.; Mandolini, L.; Ungaro, R. Tetrahedron 1995, 57, 591.
11. Geraci, C.; Piattelli, M.; Neri, P. Tetrahedron Lett. 1995,36,5429.
12. Yamamoto, H.; Shinkai, S. Cheni. Lett. 1994, 1115.
13. (a) Ghidini, E.; Ugozzoli, F.; Ungaro, R.; Harkema, S.; Abu ElFadl, A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1990, 112, 6979.
14. (b) Brzozka, Z.; Lammerink, B.; Reinhoudt, D. N.; Ghidini, E.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1993, 1037.
15. Casnati, A.; Pochini, A'.; Ungaro, R.; Bocchi, C.; Ugozzoli, F.; Egberink, R. J. M.; Struijk, H.; Lugtenberg, R.; de Jong, F.; Reinhoudt, D. N. Chem. Eur. J. 1996, 2, 436.
16. (a) Ungaro, R.; Casnati, A.; Ugozzoli, F.; Pochini, A.; Dozol, J.F.; Hill, C.; Rouquette, H. Angew. Chem., Int. Ed. Engl. 1994,33,1506.
17. (b) Casnati, A.; Pochini, A.; Ungaro, R.; Ugozzoli, F.; Arnaud, F.; Fanni, S.; Schwing, M.-J.; Egberink, R. J. M.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 2767.
18. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
19. Arduini, A.; Casnati, A.; Dodi, L.; Pochini, A.; Ungaro, R. J. Chem. Soc., Chem. Commun. 1990, 1597.
20. Asfari, Z.; Astier, J.-P.; Bressot, C.; Estienne, J.; Pepe, G.; Viccns, J. J. Ind. Phenom. Mol. Recognit. 1994, 19, 291.
21. Amaud-Neu, F.; Caccamese, S.; Fuangswasdi, S.; Pappalardo, S.; Parisi, M. F.; Petringa, A.; Principale, G. J. Org. Chem. 1997, 62, 8041.
22. Tsukube, H.; Uenishi, J.; Higaki, H.; Kikkawa, K.; Tanaka, T.; Wakabayashi, S.; Oae, S. J. Org. Chem. 1993, 58, 4389.
23. Zhong, Z.-L.; Tang, C.-P.; Wu, C.-Y.; Chen, Y.-Y. J. Chem. Soc., Chem. Commun. 1995, 1737.
24. Yamamoto, H.; Sakaki, T.; Shinkai, S. Chem. Lett. 1994, 469.
25. (a) Bottino, F.; Giunta, L.; Pappalardo, S. J. Org. Chem. 1989, 54,5407.
26. (b) Shinkai, S.; Otsuka, T.; Araki, K.; Matsuda, T. Bull. Chem. Soc. Jpn. 1989, 62, 4055.
27. (a) Pappalardo, S.; Giunta, L.; Foti, M.; Ferguson, G.; Gallagher, J. F.; Kaitner, B. J. Org. Chem. 1992, 57, 2611.
28. (b) Ferguson, G.; Gallagher, J. F.; Giunta, L.; Neri, P.; Pappalardo, S.; Parisi, M. J. Org. Chem. 1994, 59, 42.
29. For a preliminary communication on the synthesis of 1,2alternate (1,2)-calix[4]crowns, see: Pappalardo, S.; Petringa, A.; Parisi, M. F.; Ferguson, G. Tetrahedron Lett. 1996, 37, 3907.
30. Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 1996,37,1493.
31. Jaime, C.; de Mendoza, J.; Prados, P.; Nieto, P. M.; Sanchez, C. J. Org. Chem. 1991, 56, 3372.
32. Pappalardo, S. New J. Chem. 1996, 20, 465 and references therein.
33. Arnaud-Neu, F.; Böhmer, V.; Guerra, L.; McKervey, M. A.; Paulus E. F.; Rodriguez, A.; Schwing-Weill, M.-J.; Tabatabai, M.; Vogt, W. J. Phys. Org. Chem. 1992, 5, 471.
34. Pappalardo, S.; Ferguson, G.; Neri, P.; Rocco, C. J. Org. Chem. 1995, 60, 4576.
35. For π-donor participation in cation complexation by calix[4]-arenes, see: Ikeda, A.; Shinkai, S. J. Am. Chem. Soc. 1994,116, 3102.
36. Ugozzoli, F.; Ori, O.; Casnati, A.; Pochini, A.; Ungaro, R.; Reinhoudt, D. N. Supramol. Chem. 1995, 5, 179.
37. Grell, E.; Funck, T.; Eggers, F. In Membranes; Eisenmann, G., Ed.; M. Dekker: New York, 1975; Vol. 3, p 1.
38. Arnaud-Neu, F.; Deutsch, N.; Fanni, S.; Schwing-Weill, M.-J.; Casnati, A.; Ungaro, R. Gazz. Chim. Ital. 1997, 127, 693.
39. Ouchi, M.; Inoue, Y.; Kanzaki, T.; Hakushi, T. J. Org. Chem. 1984, 49, 1408.
40. Gutsche, C. D.; Iqbal, M. Org. Synth. 1989, 68, 234.
41. Sheldrich, G. M. SHELXS86. Program for the solution of crystal structures, University of Göttingen, Germany.
42. Gabe, E. J.; Le Page, Y.; Charland, J.-P.; Lee, F. L.; White, P. S. J. Appl. Crystallogr. 1989, 22, 384.
43. Sheldrich, G. M. SHELXS93. Program for the solution of crystal structures, University of Göttingeri, Germany.
44. ORTEP-A Fortran Thermal Ellipsoid Plot Program: Technical Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN.
45. Spek, A. L. PLATON Molecular Geometry Program, July 1995 version, University of Utrecht, Utrecht, Holland.
46. Sheldrich, G. M. SHELXL93. Program for the solution of crystal structures. University of Göttingen, Germany.
47. Pedersen, C. J. Fed. Proc. Fed. Am. Soc. Expl. Biol. 1968, 27, 1305.
48. Arnaud-Neu, F.; Schwing-Weill, M.-J.; Ziat, K; Cremin, S.; Harris, S. J.; McKervey, M. A. New J. Chem. 1991, 15, 33.
49. Arnaud-Neu, F.; Barrett, G.; Harris, S. J.; Owens, M.; McKervey, M. A.; Schwing-Weill, M.-J.; Schwinte, P. Inorg. Chem. 1993, 32, 2644.
50. Haeringer, M.; Schwing, J. P. Bull. Soc. Chim. Fr. 1967,9, 708.
51. Vetrogon, V. I.; Lukyanenko, N. G.; Schwing-Weill, M.-J.; Arnaud-Neu, F. Talanta, 1994, 41, 2105.
52. Tremillon, B. Chemistry in Nonaqueous Solvents; PUF: Paris, 1971.
53. Arnaud-Neu, F.; Barrett, G.; Fanni, S.; Marrs, D.; McGregor, W.; McKervey, M. A.; Schwing-Weill, M.-J.; Vetrogon, V.; Wechsler, S. J. Chem. Soc., Perkin Trans. 2 1995, 453.