Studies on photochemistry of aromatic hydrocarbons V: Photochemical reaction of chlorobenzene with nitrogen oxides in air

The investigations on the photochemical reaction of chlorobenzene with nitrogen oxides in air were carried out using the reaction vessels made of Pyrex glass and quartz, respectively. The irradiation of chlorobenzene in the Pyrex glass vessel gave m-chloronitrobenzene, 2-chloro-6-nitrophenol, 2-chloro-4-nitrophenol and 4-chloro-2-nitrophenol, while the irradiation of chlorobenzene in the quartz vessel resulted in m-chloronitrobenzene, p-nitrophenol, 2-chloro-4-nitrophenol, 3-chloro-2-nitrophenol, 3-chloro-6-nitrophenol and 3-chloro-4-nitrophenol.The formation mechanism of these chloronitrophenols was considered using the theory of the nitro-nitrite rearrangement of chloronitrobenzenes.