Abstract
The synthesis and properties of upperrim Schiff base calix[4]arenes are described in thisarticle. Tetrakis-p-bromomethylcalix[4]arene(1) reacts with hexamethylenetetramine to givetetrakis-p-formylcalix[4]arene (2) in highyield. Then upper rim Schiff base calix[4]arenes 3 can be easily synthesized by 2 reacting withappropriate alkylamines. The complexation ability of3 toward transition metals Pb2+, Cu2+and Co2+ was studied by UV-VIS spectrophotometry.
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V. Böhmer: Angew. Chem. Int. Ed. Engl. 34, 713 (1994). (b) C. D. Gutsche: Calixarenes, Monographs in Supramolecular Chemistry, Vol. 1; J. F. Stoddart (ed.); The Royal Society of Chemistry: Cambridge (1989). (c) C. D. Gutsche: Calixarenes Revisited, Ibid, (1998).
S. E. J. Bell, J. K. Browne, V. McKee, M. A. McKervey, J. F. Malone, M. O'Leary, A. Walker, F. Arnaud-Neu, O. Boulangeot, O. Mauprivez, and M.-J. Schwing-Weill: J. Org. Chem. 63, 489 (1998). (b) 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. Eur. J. 2, 436 (1996). (c) E. Ghidini, F. Ugozzoli, R. Ungaro, S. Harkema, A. A. El-Fadl, and D. N. Reinhoudt: J. Am. Chem. Soc. 112, 6979 (1990).
Y. Kubo, S. Maeda, S. Tokita, and M. Kubo: Nature 382, 522 (1996). (b) R. K. Castellano, B. H. Kim, and J. Reberk, Jr.: J. Am. Chem. Soc. 119, 12671 (1997).
R. Seangprasertkij, Z. Asfari, F. Arnaud, and J. Vicens: J. Org. Chem. 59, 1741 (1994). (b) R. Seangprasertkij, Z. Asfari, F. Arnaud, J. Weiss, and J. Vicens: J. Incl. Phenom. 14, 141 (1992). (c) W.-C. Zhang and Z.-T. Huang: Synthesis 1073 (1997).
C. D. Gutsche and L.-G. Lin: Tetrahedron 42, 1633 (1986).
V. I. Vetrogon, N. G. Lukyanenko, M.-J. Schwing-Weill, and F. Arnaud-Neu: Talanta 41, 2105 (1994).
J.-D. van Loon, A. Arduini, L. Coppi, W. Verboom, A. Pochini, R. Ungaro, S. Harkema, and D. N. Reinhoudt: J. Org. Chem. 55, 5639 (1990).
A. Arduini, M. Fabbi, M. Mantovani, L. Mirone, A. Pochini, A. Secchi, and R. Ungaro: J. Org. Chem. 60, 1454 (1995).
For a review, see S. J. Angyal: Org. React. 8, 197 (1954).
C. D. Gutsche and L. J. Bauer: J. Am. Chem. Soc. 107, 6052 (1985).
C. Jaime, J. de Mendoza, P. Prados, P. M. Nieto, and C. Sánchez: J. Org. Chem. 56, 3372 (1991).
R. D. Shannon: Acta Crystallogr. A 32, 751 (1974).
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Guo, TD., Zheng, QY., Yang, LM. et al. Synthesis and Properties of Upper Rim Schiff Base Calix[4]arenes. Journal of Inclusion Phenomena 36, 327–333 (2000). https://doi.org/10.1023/A:1008006600696
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DOI: https://doi.org/10.1023/A:1008006600696