Synthesis and Reactions of Calix[4]arene Bisanhydrides(1)

The tetrabenzyl ether, tetra-p-bromobenzenesulfonate, and tetra-p-methylbenzenesulfonate of p-carboxymethylcalix[4]arene in the 1,3-alternate conformation have been converted to the corresponding bisanhydrides. Reactions of the bisanhydrides with alcohols or amines afford calix[4]arenes carrying two carboxymethyl and two carboalkoxymethyl or two amidomethyl groups on the upper rim positions. The substitution pattern that is established confers molecular chirality on the calixarenes.