Photooxidation of DDT and DDE

The pesticide DDT [1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane] and its metabolite DDE [1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene] can be photooxidized in methanol. Photolytic generation of free radicals that may abstract hydrogen from solvent, react with oxygen, or abstract hydrogen from unreacted substrate occurs. Further decomposition of short-lived intermediates yields many compounds. Oxidation products include benzoic acids, aromatic ketones, and chlorinated phenols. The DDE also undergoes photocyclization to give dichlorofluorene derivatives.