Effect of the alkylidene spacer and the p-tert-butylthiacalix[4]arene macrocyclic platform on the reactivity of the hydroxyl groups in the acylation reaction

Abstract

A series of cone and 1,3-alternate p-tert-butylthiacalix[4]arenes tetrasubstituted at the lower rim simultaneously by the amide, ester, and carboxyl functions were synthesized. The reactivity of the synthesized compounds depends on the length of the alkylidene spacer. The N-(hydroxyethyl)amide derivatives do not react with succinic anhydride, whereas the N-(3-hydroxypropyl)amide derivatives react to form acylation products.