Synthesis and Conformational Characteristics of Benzyl-Substituted p-tert-Butylcalixarenes

摘要

(m-Methylbenzyloxy)-, bis(p-methylbenzyloxy)-, and bis(m-methylbenzyloxy)-p-tert-butylcalix [4]-arenes were prepared by reactions of p-tert-butylcalix[4] arene with p- and m-methylbenzyl bromides in the presence of alkali metal carbonates. Silylation of these derivatives gave (m-methylbenzyloxy)bis(trimethylsilyloxy)-, bis (m-methylbenzyloxy)bis(trimethylsilyloxy)-, and bis(p-methylbenzyloxy)bis(trimethylsilyl-oxy)-p-tert-butylcalix[4]arenes. With phase-transfer catalysis, bis(p-methylbenzyloxy)bis(2-propenyloxy)-and bis(m-methylbenzyloxy)bis(2-propenyloxy)-p-tert-butylcalix[4]arenes were obtained. Alkylation of the mono-substituted calixarene yields the corresponding trisubstituted derivative.