A NEW SYNTHESIS OF OXACALIX[3]ARENE MACROCYCLES AND ALKALI-METAL-BINDING STUDIES

The title oxacalix[3]arene macrocycles 1 have been synthesized in yiel ds of 12-32% by an acid-catalyzed, high-dilution condensation of 2,6-b is(hydroxymethyl)-p-subtituted-phenols, where R = t-Bu, i-Pr, Et, Me, and Cl. The macrocycles are isolated in high purity without chromatogr aphy, as the sodium or potassium,salts of their monoanions. Metal-bind ing studies indicate that, Like the related calixarenes, the oxacalix[ 3]arenes bind alkali metals only in the presence of base (Na(+)approxi mate to K+ > Li+).