Organic peroxides containing functional groups. Part I. The preparation and properties of some α-oxo-hydroperoxides

Abstract

α-Oxo-hydroperoxides have been prepared by the low-temperature base-catalysed autoxidation of methyl isopropyl ketone, di-isopropyl ketone, and 2-methylcyclohexanone. The effect of variations of solvent and base on these autoxidation reactions has been studied. The α-oxo-hydroperoxide structure has been confirmed, and derivatives of both the hydroperoxide and carbonyl functions have been prepared. The product of the decomposition of 2-hydroperoxy-2-methylcyclohexanone has been isolated and identified as 6-oxoheptanoic acid. This product has been shown to result from both the base-catalysed and the uncatalysed thermal decomposition, and the mechanism of its formation is discussed.