Photochemistry of 1-nitro-2-phenylnaphthalene available to the environment

Photolysis (254 nm, 72h) of 1-nitro-2-phenylnaphthalene $\text{1}$ in methanol gave 2-phenyl-1,4-naphthoquinone-4-monoxime $\text{2}$, 2,2′-diphenyl-4,4′-binaphth-1,1′-diol $\text{3}$ and 2,2′-diphenyl-4,4′-binaphth-1,1′-dione $\text{4}$. Straightforward reactions available to the environment account for the formation of the products: (a) isomerisation of the nitro compound into a nitrite ester followed by either (a) migration of the nitroso group and isomerisation into the oxime $\text{2}$ or (b) oxidative coupling and solvolysis into the binaphthol $\text{3}$ and followed by oxidation into the binaphthone $\text{4}$.