Synthesis and heteronuclear inclusion properties of a novel thiacalix[4]arene-based hard-soft receptor with 1,3-alternate conformation

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 68, Issue 1, 2010, Pages 99-108

  Ni, Xin Long ^a   Tomiyasu, Hirotsugu ^a   Shimizu, Tomoe ^a   Pérez Casas, Carol ^a   Xi, Zeng ^b   Yamato, Takehiko ^a  

^a SAGA UNIVERSITY   (Japan)

^b GUIZHOU UNIVERSITY   (China)

Author keywords

Conformation; Hard soft receptors; Ionophores; Metal complexation; O alkylation; Thiacalix 4 arene

Indexed keywords

EID: 79954422117     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-010-9740-5     Document Type: Article

References (42)

1. Kumagai, J., Hasegawa, M., Miyanari, S., Sugawa, Y., Sato, Y., Hori, T., Ueda, S., Kamiyama, H., Miyano, S.: Facile synthesis of p-tert-butylthiacalix[4]arene by the reaction of p-tert-butylphenol with elemental sulfur in the presence of a base. Tetrahedron Lett. 38, 3971-3972 (1997).
2. Iki, N., Kabuto, C., Fukushima, T., Kumagai, H., Takeya, H., Miyanari, S., Miyashi, T., Miyano, S.: Synthesis of p-tert-butylthiacalix[4]arene and its inclusion property. Tetrahedron 56, 1437-1443 (2000).
3. Lhoták, P.: Chemistry of Thiacalixarenes. Eur. J. Org. Chem. 8, 1675-1692 (2004).
4. For review, see: Gutsche, C. D.: Calixarenes. In: Stoddart, J. F. (ed.) Monographs in Supramolecular Chemistry. The Royal Society of Chemistry, Cambridge (1989).
5. Vicens, J., Böhmer, V.: Calixarenes: a versatile class of macrocyclic compounds. Kluwer Academic Publishers, Dordrecht, Boston (1991).
6. Ikeda, A., Shinkai, S.: On the origin of high ionophoricity of 1, 3-alternate calix[4]arenes: pi.-donor participation in complexation of cations and evidence for metal-tunneling through the calix[4]arene cavity. J. Am. Chem. Soc. 116, 3102-3110 (1994).
7. Koh, K. N., Araki, K., Shinkai, S., Asfari, Z., Vicens, J.: Cation binding properties of a novel 1, 3-alternate calix[4]biscrown. Formation of 1: 1 and 1: 2 complexes and unique cation tunneling across a calix[4]arene cavity. Tetrahedron Lett. 36, 6095-6098 (1995).
8. Iwamoto, K., Shinkai, S.: Synthesis and ion selectivity of all conformational isomers of tetrakis[(ethoxycarbonyl)methoxy]calix[4]arene. J. Org. Chem. 57, 7066-7073 (1992).
9. Pappalardo, S., Ferguson, G., Neri, P., Rocco, C.: Synthesis and complexation studies of regioisomers and conformational isomers of p-tert-butylcalix[4]arene bearing pyridine or pyridine N-oxide pendant groups at the lower rim. J. Org. Chem. 60, 4576-4584 (1995).
10. De Danil, N., Angela, F., Piro, O. E., Pulcha, S., Lupe, E., Aguilar, C., Adolfo, F., Al-Rawi, N., Catellano, E. E., Sueros, V., Felix, J.: Solution thermodynamics of geometrical isomers of pyridinocalix[4]arenes and their interaction with the silver cation. The X-ray structure of a 1: 1 complex of silver perchlorate and acetonitrile with 5, 11, 17, 23-tetra-tert-butyl-[25, 26, 27, 28-tetrakis(2-pyridylmethyl)oxy]calix[4]arene. J. Chem. Soc. Faraday Trans. 94, 3097-3104 (1998).
11. Shinkai, S., Fujimoto, K., Otsuka, T., Ammon, H.-L.: Syntheses and ion selectivity of conformational isomers derived from calix[4]arene. J. Org. Chem. 57, 1516-1523 (1992).
12. Yamato, T., Zhang, F., Kumamaru, K., Yamamoto, H.: Synthesis, conformational studies and inclusion properties of tetrakis[(2-pyridylmethyl)oxy]thiacalix[4]arenes. J. Incl. Phenom. Macrocycl. Chem. 42, 51-60 (2002).
13. Pérez-Casas, C., Yamato, T.: Hard-soft receptors, tetrakis[(N, N-diethylaminocarbonyl)methoxy]thiacalix[4]arene derivatives with cone and 1, 3-alternate conformation. J. Incl. Phenom. Macrocycl. Chem. 53, 1-8 (2005).
14. Lehn, J.-. M.: Supramolecular Chemistry: Concepts and Perspectives. VCH, Weinheim, Germany (1995).
15. Lamartine, R., Bavoux, C., Vocanson, F., Martin, A., Senlis, G., Perrin, M.: Synthesis, X-ray crystal structure and complexation properties towards metal ions of new thiacalix[4]arenes. Tetrahedron Lett. 42, 1021-1024 (2001).
16. Pérez-Casas, C., Yamamoto, H., Yamato, T.: Regioselective synthesis of distal-di-O-alkoxytetrathiacalix[4]arenes by a protection-deprotection method using benzyl groups. J. Chem. Research. 694-696 (2007).
17. Iwamoto, K., Yanagi, A., Araki, K., Shinkai, S.: Syntheses of new isomers from p-t-Butylcalix[4]arene. Strategies for regioselective alkylation on the lower rim. Chem. Lett. 473-476 (1991).
18. Iwamoto, K., Araki, K., Shinkai, S.: How is the 1, 2-alternate conformer formed in tetra-O-alkylation of p-tert-butylcalix[4]arene? J. Chem. Soc. Perkin Trans. 1, 1611-1613 (1991).
19. Iwamoto, K., Araki, K., Shinkai, S.: Conformations and structures of tetra-O-alkyl-p-tert-butylcalix[4]arenes. How is the conformation of calix[4]arenes immobilized? J. Org. Chem. 56, 4955-4962 (1991).
20. Araki, K., Iwamoto, K., Shigematsu, S., Shinkai, S.: On the origin of the distal vs. proximal regioselectivity in di-O-alkylation of calix[4]arenes. Chem. Lett. 1095-1098 (1992).
21. Iwamoto, K., Shinkai, S.: Synthesis and ion selectivity of all conformational isomers of tetrakis[(ethoxycarbonyl)methoxy]calix[4]arene. J. Org. Chem. 57, 7066-7073 (1992).
22. 1H-NMR studies of flexible tetraalkylated calix[4]arenes. J. Am. Chem. Soc. 113, 2385-2392 (1991).
23. Yamato, T., Saruwatari, Y., Yasumatsu, M. Ide, S.: Synthesis and conformational studies of regio- and conformational isomers derived from O-benzylation of tetrahydroxy[3. 1. 3. 1]metacyclophanes. Eur. J. Org. Chem. 309-316 (1998).
24. Hanessian, S., Lia k, T. J., Vanasse, B.: Facile cleavage of benzyl ethers by catalytic transfer hydrogenation. Synthesis 396-397 (1981).
25. Pearlman, W. M.: Noble metal hydroxides on carbon nonpyrophoric dry catalysts. Tetrahedron Lett. 8, 1663-1664 (1967).
26. ®) catalysis in synthesis. Synthesis 513-531 (1986) and references therein.
27. Yamato, T.: Perfluorinated resinsulfonic acid (Nafion-H) catalysis in organic synthesis. J. Synth. Org. Chem. Jpn. 53, 487-499 (1995).
28. Olah, G. A., Prakash, G. K. S., Iyer, P. S., Tashiro, M., Yamato, T.: Nafion-H catalyzed de-tert-butylation of aromatic compounds. J. Org. Chem. 52, 1881-1884 (1987).
29. Yamato, T., Hideshima, C., Tashiro, M., Prakash, G. K. S., Olah, G. A.: Organic reactions catalyzed by solid superacids. 10. Perfluorinated sulfonic acid resin (Nafion-H) catalyzed ring closure reaction of 2, 2′-diaminobiphenyls. A preparative route to carbazoles. J. Org. Chem. 56, 6248-6250 (1991).
30. Miyazawa, A., Tsuge, A., Yamato, T., Tashiro, M.: Synthesis of 4, 5-dimethyl-, 4, 5, 9-trimethyl-, and 4, 5, 9, 10-tetramethylpyrene. J. Org. Chem. 56, 4312-4314 (1991).
31. Miyazawa, A., Yamato, T., Tashiro, M.: A new synthetic route to 4-alkylpyrenes from 2, 7-di-tert-butyl-trans-10b, 10c-dimethyl-10b, 10c-dihydropyrenes. J. Org. Chem. 56, 1334-1337 (1991).
32. Yamato, T., Miyazawa, A., Tashiro, M.: Medium-sized cyclophanes, 31. synthesis and electrophilic substitution of 8-substituted [2]metacyclo[2](1, 3)pyrenophanes. J. Chem. Soc. Perkin Trans. 1, 3127-3137 (1993).
33. Yamato, T., Sakaue, N., Shinoda, N., Matsuo, K.: Selective preparation of polycyclic aromatic hydrocarbons. Part 4. A new synthetic route to anthracenes from diphenylmethanes using Friedel-crafts intramolecular cyclization. J. Chem. Soc. Perkin Trans. 1, 1193-1199 (1997).
34. Iki, N., Marumi, F., Fujimoto, T., Morohashi, N., Miyano, S.: Selective synthesis of three conformational isomers of tetrakis[(ethoxycarbonyl)methoxy]thiacalix[4]arene and their complexation properties towards alkali metal ion. J. Chem. Soc. Perkin Trans. 2, 2745-2750 (1998).
35. Iki, N., Morohashi, M., Narumi, F., Miyano, S.: High complexation ability of thiacalixarene with transition Mmtal ions. The effects of replacing methylene bridges of tetra(p-t-butyl)calix[4]arenetetrol by epithio groups. Bull. Chem. Soc. Jpn. 71, 1597-1603 (1998).
36. Iki, N., Kumagai, H., Morohashi, N., Ejima, K., Hasegawa, M., Miyanari, S., Miyano, S.: Selective oxidation of thiacalix[4]arenes to the sulfinyl- and sulfonylcalix[4]arenes and their coordination ability to metal ions. Tetrahedron Lett. 39, 7559-7562 (1998).
37. Iki, N., Morohashi, N., Narumi, F., Fujimoto, T., Suzuki, T., Miyano, S.: Novel molecular receptors based on a thiacalix[4]arene platform. Preparations of the di- and tetracarboxylic acid derivatives and their binding properties towards transition metal ions. Tetrahedron Lett. 40, 7337-7341 (1999).
38. Morohashi, N., Hattori, T., Yokomakura, K., Kabuto, C., Narumi, F., Fujimoto, T., Suzuki, T., Miyano, S.: Dinuclear titanium(IV) complex of p-tert-butylthiacalix[4]arene as a novel bidentate Lewis acid catalyst. Tetrahedron Lett. 43, 7769-7772 (2002).
39. Vögtle, F.: Cyclophane Chemistry. Wiley, New York (1993).
40. Tashiro, M., Yamato, T.: Metacyclophanes and related compounds. 1. Preparation and nuclear magnetic resonance spectra of 8, 16-disubstituted [2. 2]metacyclophanes. J. Org. Chem. 46, 4556-4562 (1981).
41. Tashiro, M., Yamato, T.: Metacyclophanes and related compounds. 8. Preparation and reaction of 8, 16-diformyl[2. 2]metacyclophanes. J. Org. Chem. 48, 1461-1468 (1983).
42. Benesi, H. A., Hildebrand, J. H.: A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71, 2073-2707 (1949).