Dimercuration of Calix[4]arenes: Novel Substitution Pattern in Calixarene Chemistry

Abstract

A mercuration reaction of tetrapropoxycalix[4]­arene immobilized in the <i>cone</i> conformation gave a mixture of two dimercurated products (<i>meta</i>,<i>meta</i> and <i>meta</i>,<i>para</i>) in approximately a 1:1 ratio. Both regioisomers represent inherently chiral compounds, which makes them very attractive for design of novel receptors. As demonstrated by Pd-catalyzed arylation, the different reactivity of HgCl functions in the <i>meta</i>,<i>para</i>-disubstituted isomer opens the door for regioselective introductions of two different functional groups to achieve a substitution pattern so far unknown in calixarene chemistry