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Upon irradiation with a xenon lamp through a Pyrex filter (cut-off below 290 nm), olefinic compounds such as trans-stilbene, cyclohexene, 4, 5-dibromocyclohexene and aldrin reacted with nitrogen dioxide, an air pollutant which induces photochemical smog, in air and gave the corresponding epoxides in good yields, while phenanthrene gave 9, 10-phenanthrenequinone and 9-hydroxy-10-nitrophenanthrene. Furthermore, the photochemical and dark reactions of phenanthrene 9, 10-oxide with nitrogen dioxide in air both resulted in the same products as above. Therefore, phenanthrene 9, 10-oxide seems to be an intermediate in the photochemical reaction of phenanthrene with nitrogen dioxide in air

Studies on photochemical reactions of air pollutants. VIII. Photochemical epoxidation of olefins with NO2 in a solid-gas phase system.