P-TRIALLYLCALIX[4]ARENE - THE FINAL MEMBER OF THE P-ALLYLCALIX[4] ARENES

The heat-induced Claisen rearrangement of calix[4]arene triallyl ether 6a produced the title compound, p-triallylcalix[4]arene (7). The tria llyl ether 6a was prepared from calix[4]arene 1,3-diallyl ether (1a) i n a three-step process. Benzoylation of 1,3-diallyl ether 1a, under se parate 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 derivative s are discussed. Further study of this four-step conversion for other calix[4]arene trialkyl ether derivatives is also presented. Copyright (C) 1996 Elsevier Science Ltd.