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

Article abstract of DOI:10.1246/bcsj.54.2352

The photoreaction of anthracene witn 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 radical as well as their reactivities.