Multifold ring closing metathesis reactions in the formation of resorcin[4]arene cavitands

Abstract

The formation of the resorcin[4]arene cavitands using the ring closing metathesis reaction (RCM) in perallylated resorcin[4]arenes was investigated. The formation of resorcinarene cavitands offers unique molecular platforms for host–guest chemistries, sensor development, metal complexation, as well as new polymers and self-assembled systems, and as potential reaction sites, and novel catalytic platforms. In this manuscript we show that cavitand formation by the RCM reaction depends, to a large extent, on the conformation and the substituents on the upper and lower rim of the perallylated resorcin[4]arenes. The perallylation of the octahydroxy compounds disrupted the intramolecular hydrogen bonds causing a dynamic shift in the conformer equilibrium.