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

A mercuration reaction of tetrapropoxycalix[4]arene immobilized in the cone conformation gave a mixture of two dimercurated products (meta,meta and meta,para) 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 meta,para-disubstituted isomer opens the door for regioselective introductions of two different functional groups to achieve a substitution pattern so far unknown in calixarene chemistry.