Synthesis, structure, and extraction properties of paco-calix[4]arene crown-6 ethers

Journal of Inclusion Phenomena

Volumn 43, Issue 1-2, 2002, Pages 55-64

  Sachleben, Richard A ^a   Bryan, Jeffrey C ^a   Das, Goutam ^a,b   Descazeaud, Tanneguy ^a   Sun, Yunfu ^a   Moyer, Bruce A ^a  

^a OAK RIDGE NATIONAL LABORATORY   (United States)

^b Betz Dearborn Division   (United States)

Author keywords

Calyx 4 arene; Cesium; Crown ether; Crystal structure; NMR; Solvent extraction

Indexed keywords

CESIUM; CROWN ETHER DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; METAL EXTRACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0346394857     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1020474827521     Document Type: Article

References (41)

1. (a) C.D. Gutsche: Calixarenes Revisited; in J.F. Stoddard (ed.), Monographs in Supramolecular Chemistry, The Royal Society of Chemistry, Cambridge (1998);
2. (b) J. Vicens and V. Böhmer (eds.), Calixarenes, A Versatile Class of Macrocyclic Compounds, Kluwer, Dordrecht (1991).
3. C. Alfieri, E. Dradi, A. Pochini, R. Ungaro, and G.D. Andreetti: J. Chem. Soc., Chem. Commun. 1075 (1983).
4. (a) S. Shinkai: Tetrahedron 49, 8933 (1993);
5. (b) V. Böhmer: Angew. Chem. 106, 785 (1995) [Angew. Chem. Int. Ed. Engl. 34, 713 (1995)];
6. (c) P. Timmerman, W. Verboom, and D.N. Reinhoudt: NATO ASI Ser. Ser. E 320, 245 (1996);
7. (d) A. Casnati: Gazz. Chim. Ital. 127, 637 (1997);
8. (e) S. Shinkai: Chem. Rev. 97, 1713 (1997).
9. C.D. Gutsche, B. Dhawan, F.A. Levine, K.H. No, and L.J. Bauer: Tetrahedron 39, 409 (1983).
10. K. Iwamoto, K. Asaki, and S. Shinkai: J. Org. Chem. 56, 4955 (1991).
11. (a) C.D. Gutsche and P.A. Reddy: J. Org. Chem. 56, 4783 (1991);
12. (b) L.C. Groenen, J.-D. van Loon, W. Verboom, S. Harkema, A. Casnati, R. Ungaro, A. Pochini, F. Ugozzoli, and D.N. Reinhoudt: J. Am. Chem. Soc. 113, 2385 (1991);
13. (c) W. Verboom, S. Datta, Z. Asfari, S. Harkema, and D.N. Reinhoudt: J. Org. Chem. 57, 5394 (1992).
14. E. Ghidini, F. Ugozzoli, R. Ungaro, S. Harkema, A.A. El-Fadl, and D.N. Reinhoudt: J. Am. Chem. Soc. 112, 6979 (1990).
15. A. Casnati, A. Pochini, R. Ungaro, C. Bocchi, F. Ugozzoli, R.J.M. Egberink, H. Struijk, R. Lugtenberg, F. de Jong, and D.N. Reinhoudt: Chem. European J. 2, 436 (1996).
16. (a) T.J. Haverlock, P.V. Bonnesen, R.A. Sachleben, and B.A. Moyer: Radiochim. Acta 76, 103 (1997);
17. (b) P.V. Bonnesen, L.H. Delmau, B.A. Moyer, and R.A. Leonard: Solvent Extr. Ion Exch. 18(6), 1079-1108 (2000);
18. (c) B.A. Moyer, P.V. Bonnesen, R.A. Sachleben, and D.J. Presley: USP 6,174,503, Jan. 16, 2001.
19. Comparison of different conformers of 25,27-bis-2-propoxycalix[4]arene crown-6 ethers in ion-selective electrodes has been reported: C. Bocchi, M. Careri, A. Casnati, and G. Mori: Anal. Chem. 67, 4234 (1995).
20. The synthesis of 2a has been previously reported: A. Casnati, A. Pochini, R. Ungaro, F. Ugozzoli, F. Arnaud, S. Fanni, M.-J. Schwing, R.J.M. Egberink, F. de Jong, and D.N. Reinhoudt: J. Am. Chem. Soc. 117, 2767 (1995).
21. (a) G. Balacco: J. Chem. Inf. Comput. Sci. 34, 1235 (1994);
22. (b) G. Balacco: Mol. Biol. Today 1, 23 (2000).
23. K. Harms: XCAD4, Universität Marburg, Germany, 1995.
24. SHELXTL (Version 5.1, IRIX), Bruker AXS, Madison, Wisconsin, 1997.
25. A.L. Spek: PLATON: A Multi-Purpose Crystallographic Tool, Universiteit Utrecht, The Netherlands, 1999.
26. H.D. Flack: Acta Crystallogr. A39, 876 (1983).
27. T.W. Green and P.G.M. Wuts: Protective Groups in Organic Synthesis, 2nd ed., Wiley, New York (1991).
28. C.D. Gutsche, F.A. Levine, and P.K. Sujeeth: J. Org. Chem. 50, 5802 (1985).
29. The syn isomer crystallized from the mother liquor upon standing; however, this compound is more readily prepared directly from calix[4]arene (see ref. 10).
30. (a) S.G. Bott, A.W. Coleman, and J.L. Atwood: J. Incl. Phenom. 5, 747 (1987);
31. (b) S. Shang, D.V. Khasnis, H. Zhang, A.C. Small, M. Fan, and M. Lattman: Inorg. Chem. 34, 3610 (1995); P. Rao, O. Enger, E. Graf, M.W. Hosseini, A. De Cian, and J. Fischer: Eur. J. Inorg. Chem. 1503, (2000).
32. (b) S. Shang, D.V. Khasnis, H. Zhang, A.C. Small, M. Fan, and M. Lattman: Inorg. Chem. 34, 3610 (1995); P. Rao, O. Enger, E. Graf, M.W. Hosseini, A. De Cian, and J. Fischer: Eur. J. Inorg. Chem. 1503, (2000).
33. P. Lhoták, L. Kaplánek, I. Stibor, J. Lang, H. Dvoráková, R. Hrabal, and J. Sykora: Tetrahedron Lett. 41, 9339 (2000).
34. J. Dale: Isr. J. Chem. 20, 3 (1980).
35. J.C. Bryan, A.P. Marchand, and A. Hazlewood: Acta Crystallogr. E 57, o13 (2001), and references therein.
36. P. Thuéry, M. Nierlich, J.C. Bryan, V. Lamare, J.-F. Dozol, Z. Asfari, and J. Vicens: J. Chem. Soc., Dalton Trans. 4191 (1997).
37. (a) J.C. Bryan, T. Chen, T.G. Levitskaia, T.J. Haverlock, C.E. Barnes, and B.A. Moyer: J. Incl. Phenom., in press.
38. (a) P. Thuéry, M. Nierlich, V. Lamare, J.-F. Dozol, Z. Asfari, and J. Vicens: J. Incl. Phenom. Mol. Recognit. Chem. 36, 375 (2000);
39. (b) P. Thuéry, M. Nierlich, Z. Asfari, J. Vicens, and J.-F. Dozol: Polyhedron 19, 1749 (2000).
40. (a) A. Casnati, E. Comelli, M. Fabbi, V. Bocchi, G. Mori, F. Ugozzoli, A.M.M. Lanfredi, A. Pochini, and R. Ungaro: Recl. Trav. Chim. Pays-Bas 112, 384 (1993);
41. (b) M. Gómez-Kaifer, P.A. Reddy, C.D. Gutsche, and L. Echegoyen: J. Am. Chem. Soc. 119, 5222 (1997).