PHOTOCHEMICAL OXYGENATION OF STYRENE BY PYRIMIDOPTERIDINE 10-OXIDE AS A CHEMICAL MIMIC OF HEMIN-CATALYZED OXYGENATION

Article abstract of DOI:10.1016/S0040-4020(01)86754-5

Irradiation of styrene (5) in the presence of pyrimido<5.4-g>pteridine 10-oxide (1) with u.v.-visible light resulted in the formation of styrene oxide (6) and phenylacetaldehyde (7) which are proved as primary metabolites of (5).Chemical and physicochemical facts showed that the photooxygenation of (5) by (1) involves an initial single-electron transfer followed by oxygen-atom transfer, accommodating the oxygenation mode of cytochrome P-450 and other hemoproteins.Comparative experiments with 3-methylpyridazine 2-oxide (3) and pyridine N-oxide (4) demonstrated the simplicity and the mechanistic characteristic of the photooxygenation by (1).