Photochemical oxygenation of olefins by heterocyclic n-oxides: mechanistic characteristics in the photochemistry of pyrimidopteridine-10-oxide

Article abstract of DOI:10.3987/COM-89-S33

A novel heterocyclic N-oxide, pyrimido<5,4-g>pteridine-10-oxide (1), oxygenates cyclohexene (4) and norbornene (9) under the photochemical conditions to give the corresponding oxidation products, (5) - (8) and (10) - (12), respectively.Experimental results clearly indicate that the photochemical oxygenation by (1) involves a single-electron transfer from the olefins (4) and (9) to the singlet-excited (1) followed by oxygen-atom transfer rather than oxene mechanism.