The photochemical reactions of 9,10-anthracenedicarbonitrile and 1,4-naphthalenedicarbonitrile in acetonitrile in the presence of bases

Irradiation of 9,10-anthracenedicarbonitrile(DCA) in MeCN-MeOH or MeCN-H2O contg. hydroxides or methoxides leads to 9-methylimino-10-anthracenecarbonitrile (isolated, but easily hydrolyzed to the corresponding amine). Minor products are polycyanated amines and 9-hydroxy-10-anthracenecarbonitrile. Irradn. in neat MeOH causes decyanation. In both cases the first step is redn. to DCA-., which persists for hours under these conditions. Evidence for the mechanism leading from the radical anion to the obsd. products is supplied.