A New Synthesis of Oxacalixarene Macrocycles and Alkali-Metal-Binding Studies

Article abstract of DOI:10.1021/jo00096a026

The title oxacalix<3>arene macrocycles 1 have been synthesized in yields of 12-32percent by an acid-catalyzed, high-dilution condensation of 2,6-bis(hydroxymethyl)-p-subtituted-phenols, where R = t-Bu, i-Pr, Et, Me, and Cl.The macrocycles are isolated in high purity without chromatography, as the sodium or potassium salts of their monoanions.Metal-binding studies indicate that, like the related calixarenes, the oxacalix<3>arenes bind alkali metals only in the presence of base (Na(1+) ca.K(1+) > Li(1+)).