The photolysis of nitrate esters dissolved in benzene or ethanol or absorbed on hlter paper occurred readily under illumination in the 265 mp t o 334 mp spectral region. Equimolar amounts of 1,4;3,6-dianhydro-D-glucitol-2,5-dinitrate and diphenylamine dissolved in absolute ethanol or benzene did not react in the dark a t 25'. Irradiation of the nitrogen-purged solutions for 2 hours a t 15' with a mercury arc followed by chromatographic separation yielded 2-nitro-, 4-nitro-, N-nitroso-, and 4-nitroso-diphenylamine together with about 4% unreacted diphenylamine and an unidentified mixture of more polar compounds. In a partial fractionation of the aromatic photoproducts approximately 80% of the original diphenylamine was recovered in the form of the monosubstituted derivatives which contained about 37% of the original ester nitrogen as C-nitro groups and 2 to 3% as C-and iV-nitroso groups.

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