OXIDATIONS BY A H2O2-VO3--PYRAZINE-2-CARBOXYLIC ACID REAGENT .1. OXIDATION OF ALKANES IN CH3CN TO PRODUCE ALKYL PEROXIDES

Alkanes (cyclohexane, hexane, heptane isomers) are effectively oxidized in CH3CN at 20-70-degrees-C by hydrogen peroxide when catalyzed by a Bu4NVO3-pyrazine-2-carboxylic acid system. Alkyl hydroperoxide is the main product; an alcohol and a ketone or an aldehyde are also formed. Under these conditions benzene is oxidized to give phenol, while alkyl benzenes yield oxygenation products both of the ring and the side chain. It has been assumed that the interaction of H2O2 with VO3- gives rise to generation of HO' radicals and other radical-like vanadium containing species that abstract a hydrogen atom from an alkane, RH. The radical R. formed reacts with O2 to produce ROO. which is then transformed to alkyl hydroperoxide.