The photoreactions of aromatic carbonyl compounds with amines. Part III. The photoreactions of fluorenone with tertiary amines

Abstract

Flash-photolysis experiments have shown that electronically excited fluorenone reacts with NN-dimethylaniline in polar solvents, to give the radical cation of the amine and the radical anion of the ketone. In benzene solution, the only radicals detected were the 9-hydroxyfluorenyl radical and the fluorenone radical anion. By the same technique, excited fluorenone was shown to react with triethylamine in both polar and non-polar solvents to give the fluorenone radical anion and the 9-hydroxyfluorenyl radical. The former radical is probably produced by dissociation of the latter radical. The photoreactions of fluorenone with amines are interpreted in terms of exciplex and radical ion intermediates.