Oxidation of Secondary Benzyl Halides to Aromatic Ketones with Singlet Oxygen Generated from trans-5-Hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl Ethaneperoxoate/t-BuOK System

The trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxoate (THDDE)/t-BuOK system has been shown to be highly effective in oxidizing a range of substituted secondary benzyl halides. Singlet molecular oxygen generated in situ by treatment of THDDE with t-BuOK acts as an effective oxidizing agent for the selective oxidation of secondary benzyl halides to the corresponding ketones regardless of the nature of the substituents on the aromatic ring, whether they are electron-donating or electron-withdrawing.