Reaction of 1,2,4,5-Tetramethyl-1,4-cyclohexadiene with Ozone − Competition between Oxidative Cleavage and Oxydehydrogenation

Treatment of 1,2,4,5-tetramethyl-1,4-cyclohexadiene (1) on polyethylene and in pentane with excess ozone afforded mixtures of the oxydehydrogenation product 2 and of the oxidative cleavage product 4 in ratios of 0.5:1 and 19:1, respecively. Epoxidation of 1 followed by ozonolysis of the epoxide 6 provided the epoxyozonide 7.