Studies on Photochemical Reactions of Air Pollutants. XIII. Formation of Nitrophenols by the Reactions of Three Toluene Oxides with Nitrogen Dioxide in Air.

Abstract

Three toluene oxides reacted with nitrogen dioxide in air to give nitrocresols. 1-Methylbenzene oxide (1) and 3-methylbenzene oxide (2) gave the same nitrocresols, including 2-methyl-6-nitrophenol (1b) and 2-methyl-4-nitrophenol (1c), while 4-methylbenzene oxide (3) gave only 4-methyl-2-nitrophenol (3b). Irradiation with a xenon lamp through a Pyrex filter (cut-off below 290 nm) did not affect the product distribution. Only 1-methylbenzene oxide (1) generated fog when it was brought into contact with nitrogen dioxide in air.