Abstract
Novel macrocyclic compounds, hexahydroxy[1.0.1.0.1.0]- (2b) and octahydroxy[1.0.1.0.-1.0.1.0]metacyclophane (2c) have been prepared in 50–70% yield by base-catalyzed condensation of 5,5′-di-tert-butyl-2,2′-dihydroxybiphenyl (1) with formaldehyde in refluxing xylene. An attempted alkylation of the flexible macrocycles 2b and 2c with ethyl bromoacetate in the presence of Cs2CO3 under acetonitrile reflux gave only one pure stereoisomer 3 and 4, respectively, while other possible isomers were not observed. The structural characterization of these products is also discussed. The two-phase solvent extraction data indicated that hexaethyl ester 3 and octaethyl ester 4 show strong metal affinity, comparable with that of the corresponding calix[n]arenes, and a high K+ selectivity was observed for octaethyl ester 4. 1H-NMR titration of hexaethyl ester 3 and octaethyl ester 4 with KSCN clearly demonstrate that a 1: 1 complex is formed which is stable on the NMR time scale.
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This paper is dedicated to the commemorative issue on the 50th anniversary of calixarenes.
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© 1994 Springer Science+Business Media Dordrecht
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Yamato, T., Yasumatsu, M., Saruwatari, Y., Doamekpor, L.K. (1994). Synthesis and Ion Selectivity of Macrocyclic Metacyclophanes Analogous to Spherand-Type Calixarenes. In: Vicens, J., Asfari, Z., Harrowfield, J.M. (eds) Calixarenes 50th Anniversary: Commemorative Issue. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0267-4_20
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DOI: https://doi.org/10.1007/978-94-011-0267-4_20
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