Oxidation of aromatic substrates. Part II. The action of ruthenium tetraoxide on some derivatives of naphthalene and its monoazaanalogues

Abstract

Although benzene and pyridine undergo rapid reactions with ruthenium tetraoxide, the products of which have not been characterised, naphthalene derivatives and their monoaza-analogues afford phthalic or pyridine-2,3-dicarboxylic acids by selective ring cleavage. A procedure which obviates losses during work-up in the presence of surface-active ruthenium dioxide is described. The analogy with ozonolysis provides a guide in predicting the behaviour of substrates on treatment with ruthenium tetraoxide.