p-Triallylcalix[4]arene: The final member of the p-allylcalix[4]arenes

Article abstract of DOI:10.1016/0040-4020(96)00786-7

The heat-induced Claisen rearrangement of calix[4]arene triallyl ether 6a produced the title compound, p-triallylcalix[4]arene (7). The triallyl ether 6a was prepared from calix[4]arene 1,3-diallyl ether (1a) in a three-step process. Benzoylation of 1,3-diallyl ether 1a, und separate reaction conditions, resulted in the formation of either one of the isomeric pair of monobenzoates 2 or 3a. The allylation of 3a and subsequent debenzoylation yielded calix[4]arene triallyl ether 6a. The synthesis and structural assignment of these calix[4]arene derivatives are discussed. Further study of this four-step conversion for other calix[4]arene trialkyl ether derivatives is also presented.