The electron transfer photooxygenation of toluene, p-chlorotoluene, p-cyanotoluene, and p-nitrotoluene sensitized by 9,10-dicyanoanthracene (DCA) and chloranil were reported. Photooxygenation of toluene and p-chlorotoluene could be sensitized by DCA or chloranil, yielding the corresponding substituted benzaldehydes and benzoic acids as products. Neither DCA nor chloranil could sensitize the photooxygenation of p-cyanotoluene and p-nitrotoluene. However, both hydrocarbons could be photooxygenated in the presence of equimolar amount of biphenyl as cosensitizer and with chloranil as sensitizer to give the corresponding substituted benzaldehydes and benzoic acids. The reaction mechanisms were discussed according to the fluorescence quenching studies and the effects on the reaction of different additives such as cosensitizer biphenyl, O2-?trap benzophenone, anhydrous salt Mg(ClO4)2 and electron donor p-dimethoxybenzene.

Key words: BENZALDEHYDE P, PHOTOSENSITIZATION, REACTION MECHANISM, PHOTOOXIDATION, METHYLBENZENE, ANTHRACENE, BENZENECARBOXYLIC ACID P, CHLOROMETHYLBENZENE, CHLORANIL, ELECTRON TRANSFER REACTION