Farbstoffsensibilisierte Photo-Oxygenierung von(−)-cis-Pulegol und (+)-Pulegon. Zur Addition von O2(1Δg) an Doppelbindungen mit allylständiger. Hydroxyl- oder Carbonyl-Gruppe

(?)-cis-Pulegol ( 1 ) and (+)-pulegone ( 2 ) readily add one mole of oxygen on dyesensitized photo-oxygenation in solution, forming almost exclusively allyl hydroperoxides. The product distributions and structures of the peroxides ( B–E ) have been derived from analysis of their reduction products. Compound 1 yielded only the diols 4, 5 and 6 , besides the epoxyketones 7 and 8 formed directly from the hydroperoxide C (proportions of 4–8 , ～21:56:13:4:6), while 2 gave the keto-alcohols 9,10 and 11 (～80:6:14) as the sole products. The course of addition of O₂(¹Δ_g) on 1 and 2 was found in all cases to be independent of solvent and photosensitizer.