Photochemical Reactions of Aromatic Compounds. XXXVI. The Photoreactions of Anthracene with Some Selected Tertiary Aromatic Amines in Polar Media

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Abstract
The photoreaction of anthracene with N,N-dimethylaniline in acetonitrile gave 9-(p-dimethylaminophenyl)9,10-dihydroanthracene in a good yield, along with 9,10-dihydroanthracene and 9,9′,10,10′-tetrahydro-9,9′-bianthryl. This photoreaction was found to depend on the polarity of the solvent as well as on its protic or aprotic nature. With N,N-dimethyl-m-toluidine, a similar 1 : 1 adduct was obtained, while the reduced anthracenes were mainly formed in the photoreactions with N,N-dimethyl-o- and p-toluidines. The mechanisms were discussed in terms of the dissociation into the ion radicals as well as their reactivities.