Synthesis of phenols with potential biological activity

ORGN 669

Zeynep Delen and Paul M. Lahti. Department of Chemistry, University of Massachusetts, Amherst, MA 01003
Phenols are considered important for biological systems due to their antioxidant properties. 2,6-Di-t-butyl phenols with varying heterocyclic rings at their para positions were synthesized using palladium and copper coupling chemistry. The crystal structures of the phenols revealed an interesting hydrogen-bonding pattern involving the nominally quite hindered phenolic OH with heterocycle nitrogen acceptors. FTIR spectra helped to differentiate apparent H-bonds from intermolecular close contacts that involve OH groups. ESR spectra of the corresponding phenoxyl radicals were examined. A UV kinetic study was carried out to compare the stabilities of the phenoxyl radicals under ambient solution conditions.