Sterically hindered o-quinone annulated with dithiete: a molecule comprising diolate and dithiolate coordination sites

Abstract

A new stable sterically hindered o-quinone annelated with a 1,2-dithiete ring was prepared by using mild conditions. The skeleton of the compound comprises diolate and dithiolate functions that have the potential to bind metals leading to the corresponding complexes. The reactivity of this compound as a ligand with respect to both coordination sites was studied. Reactions with metals indicate that the o-quinone function is reduced in the first stage to give semiquinonate and catecholate complexes. The dithiolate coordination site was involved in the reaction in a few cases only after diolate was bound. A trinuclear manganese complex with coordination on both sites was obtained and characterized by EPR spectroscopy. The electrochemical study of this quinone fused with dithiete is reported.