Oxidation of mono-phenols to para-benzoquinones: A comparative study

Abstract

The oxidation of mono-phenols to para-benzoquinones is of continuing interest due to the existence of numerous natural products containing this structural unit. The chemical reactivity of para-benzoquinones is also noteworthy, as oxidants and dienophiles in the Diels-Alder reaction. We have used for quite some time now, molecular oxygen and catalysis with [Co II(salen)] as the oxidation procedure, but felt the need for other oxidants and conditions to be of use with different phenol substrates. We now present our results on this important oxidation with a variety of oxidants, using eleven mono-phenols as substrates. The oxidants tested are cobalt, nickel, copper and vanadyl metals, with a selection of different salen type ligands. Completing this study we also investigated the use of hydrogen peroxide, OXONE®, dimethyl dioxirane and iodoxybenzoic acid. ©2008 Sociedade Brasileira de Química.