Synthesis and metal ion complexation studies of proton-ionizable calix[4]azacrown ethers in the 1,3-alternate conformation

Journal of Organic Chemistry

Volumn 65, Issue 8, 2000, Pages 2386-2392

  Kim, Jong Seung ^a   Shon, Ok Jae ^a   Ko, Jong Won ^b   Cho, Moon Hwan ^b   Yu, Ill Yong ^a   Vicens, Jacques ^c  

^a Konyang University   (South Korea)

^b Kangwon National University   (South Korea)

^c UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CROWN ETHER DERIVATIVE; METAL COMPLEX; POTASSIUM ION; TOLUENESULFONAMIDE DERIVATIVE;

ARTICLE; EXTRACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0000959851     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9912754     Document Type: Article

References (36)

1. Takagi, M.; Ueno, K. Top. Curr. Chem. 1984, 121, 39.
2. Sink, R. M.; Buster, D. C.; Sherry, A. D. Inorg. Chem. 1990, 29, 3645.
3. Delgado, R.; Frasto da Silva, J. J. R. Talanta 1982, 29, 815.
4. Reisen, A.; Zehnder, M.; Kaden, T. A. J. Chem. Soc., Chem. Commun. 1985, 1336.
5. Löhr, H.-G.; Vögtle, F. Acc. Chem. Res. 1985, 18, 65.
6. Tsukube, H.; Adachi, H.; Morosawa, S. J. Chem. Soc., Perkin Trans. 1 1989, 89.
7. Inoue, Y.; Ouchi, M.; Hosoyama, K.; Hakushi, T.; Liu, Y.; Takeda, Y. J. Chem. Soc., Dalton Trans. 1991, 1291.
8. Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2495.
9. Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017.
10. Czech, B. P.; Gebauer, C. R.; Kumar, A.; Sy-Icaza, S.; Barczak, C.; Chapoteau, E.; Babb, D. A.; Czech, A.; Bartsch, R. A. Clin. Chem. 1986, 32, 1173.
11. Vögtle, F.; Weber, E. In Host-Guest Complex Chemistry, Macrocycles; Springer-Verlag: Berlin, 1985; pp 84, 90, 189, 217.
12. (a) McDaniel, C. W.; Bradshaw, J. S.; Izatt, R. M. Heterocycles 1990, 30, 665.
13. (b) Nakamura, H.; Sakka, H.; Takagi, M.; Ueno, K. Chem. Lett. 1981, 1305.
14. (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
15. (b) Gutsche, C. D. In Synthesis of Macrocycles: Design of Selective Complexing Agents; Izatt, R. M., Christensen, J. J., Eds.; Wiley: New York, 1987; p 93.
16. (c) Calixarenes: A Versatile Class of Macrocyclic Compounds: Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991.
17. (d) Böhmer, V.; McKervey, M. A. Chemie in unserer Zeit 1991, 195.
18. (e) Gutsche, C. D. Calixarenes, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, U. K., 1989; Vol. 1.
19. (f) Gutsche, C. D. In Inclusion Compounds; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Eds.; Oxford University Press: New York, 1991; Vol. 4, pp 27-63.
20. (g) Van Loon, J.-D.; Verboom, W.; Reinhoudt, D. N. Org. Prep. Proc. Int. 1992, 24, 437-462.
21. (h) Ungaro. R.; Pochini, A. In Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H.-J., Eds.; VCH: Weinheim, Germany, 1991; pp 57-81.
22. Andreetti, G. D.; Ugozzoli, F.; Ungaro, R.; Pochini, A. In Inclusion Compounds; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Eds.; Oxford University Press: New York, 1991; Vol. 4, pp 64-125.
23. 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.
24. Kim, J. S.; Suh, I. H.; Kim, J. K.; Cho, M. H. J. Chem. Soc., Perkin Trans. 1 1998, 2307.
25. Kim, J. S.; Ohki, A.; Ueki, R.; Ishizuka, T.; Shimotashiro, T.; Maeda, S. Talanta 1999, 48, 705-710.
26. Kim, J. S.; Ohki, A.; Cho, M. H.; Kim, J. K.; Ra, D. Y.; Cho, N. S.; Bartsch, R. A.; Lee, K. W.; Oh, W. Z. Bull. Kor. Chem. Soc. 1997, 18, 1014.
27. Kim, J. S.; Lee, W. K.; Ra, D. Y.; Lee, Y. I.; Choi, W. K.; Lee, K. W.; Oh, W. Z. Microchem. J. 1998, 59, 464.
28. Kim, J. S.; Pang, J. H.; Yu, I. Y.; Lee, W. K.; Suh, I. H.; Kim, J. K.; Cho, M. H.; Kim, E. T.; D. Y. Ra. J. Chem. Soc., Perkin Trans. 2 1999, 837.
29. Kruizinga, W. H.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 5183.
30. Anelli, P. L.; Montanari, F.; Quici, S.; Ciani, G.; Sironi, A. J. Org. Chem. 1988, 53, 5292. (The reaction conditions are similar, but the workup and purification processes are somewhat different.)
31. Gokel, G. W.; Garcia, B. J. Tetrahedron. Lett. 1977, 4, 317.
32. Kimura, K.; Tanaka, M.; Iketani, S.; Shono, T. J. Org. Chem. 1987, 52, 836.
33. Bartsch, R. A.; Yang, I. W.; Jeon, E. G.; Walkowiak, W.; Charewicz, W. A. J. Coord. Chem. 1992, 27, 75.
34. (a) Gokel, G. In Crown Ethers & Cryptands; Stoddart, J. F., Ed.; The Royal Society of Chemistry: London, U. K, 1991; p 81.
35. (b) Lee, S. S.; Jung, J. H.; Yu, S. H.; Cho, M. H. Thermochim. Acta 1995, 259, 133.
36. Cho, M. H.; Seon-Woo, K. W.; Hea, M. Y.; Lee, I. C.; Yoon, C. J.; Kim, S. J. Bull. Kor. Chem. Soc. 1988, 9, 5.