Mechanism of Photolysis of p-Azido-N-methyl-N-nitrosoaniline

Abstract

The photodecomposition processes of p-azido-N-methyl-N-nitrosoaniline (1), which is expected to be used as a caged compound of nitrogen monoxide (NO), were studied in solutions at room temperature and in low-temperature matrices. Irradiation (> 350 nm) of 1 in benzene containing tetraphenylporphinatocobalt produced the corresponding Co-NO complex, implying that the photolysis of 1 gave NO. Irradiation (366 nm) of 1 in an Ar matrix at 10 K afforded IR peaks due to NO (1873 cm^-1) and the new species, which could be assigned to p-benzoquinonediimine radical. The radical was thought to be formed through the generation of nitrene, followed by the cleavage of N-N bond of the N-nitoroso group.