Photochemistry of p-Nitroacetophenone in 2-Propanol

Article abstract of DOI:10.1002/jccs.199800050

Upon irradiation in 2-propanol, p-nitroacetophenone 1 was reduced via the triplet state to p-hydroxyammoacetophenone 5 which was further reduced top-aminoacetophenone 2 and 4,4′-diacetylazobenzene 4. Similar irradiation of 5 also gave 2 and 4, and its oxidation by oxygen gave 4,4′-diacetylazoxybenzene 3. Photolysis of monomeric p-nitrosoacetophenone 6 afforded acetophenone and 3 that were not produced during the irradiation of 1 Possible photoreaction pathways were discussed on the basis of published mechanisms.