Products and Relative Reaction Rates of the Oxidation of Tocopherols With Singlet Molecular Oxygen

The relative reactivity of singlet molecular oxygen, 02(1Δg), α‐,β‐,Γ‐and δ with ‐tocopherol (vitamin E) was investigated using microwave discharge generation as a uniquely clean source of singlet oxygen and using a hydrocarbon solvent to approximate the membrane environment. The relative efficiencies of the tocopherols for O2(1Δg) were found to decrease in the order: D‐α‐tocopherol > D‐β‐tocopheroI > D–Γ‐tocopherol > D‐δ‐tocopherol. The reaction products in all cases were found to be mixtures of quinone and quinone epoxides apparently resulting from decomposition of the primary product, the hydroperoxydienone.