Selective Functionalization of Calixarenes at the Upper Rim

Article abstract of DOI:10.1021/jo00308a024

Methods are described for the selective diametrical functionalization of calix<4>arenes at the upper rim, either by the selective removal of the p-tert-butyl groups and subsequent substitution at the free phenol rings or by selective reactions at the phenol rings of dialkoxycalix<4>arenes without the tert-butyl groups.This includes selective mercuration and the synthesis of 5,17-di-tert-butyl-26,28-dimethoxy-11,23-diphenylcalix<4>arene (13), of which the crystal structure is described.The first synthesis of macrocyclic diquinones derived from calix<4>arenes (calix<4>diquinones) is described.