<i>per</i>-Hydroxylated Prism[<i>n</i>]arenes: Supramolecularly Assisted Demethylation of Methoxy-Prism[5]arene

Abstract

Methoxy-prism[5]arene <b>PrS[5]</b>^{<i><b>Me</b></i>} is demethylated by a supramolecularly assisted reaction. In the presence of a tetramethylammonium cation, <b>PrS[5]</b>^{<i><b>Me</b></i>} is demethylated by BBr₃ in high yield, while in its absence a 55/40 mixture of <b>PrS[5]</b>^{<i><b>OH</b></i>}/<b>PrS[6]</b>^{<i><b>OH</b></i>} is formed. The dealkylation of prismarenes, such as <b>PrS[6]</b>^{<i><b>R</b></i>} (R = Et, <i>n</i>Pr) and <i><b>c-</b></i><b>PrS[5]</b>^{<i><b>Me</b></i>}, can be easily obtained in high yields in the presence of BBr₃.