The photolysis of 4,5-diphenyl-3-(4-methylphenyl)-4-oxazolin-2-one in benzene or cyclohexane in the presence of singlet oxygen using UV light affords benzil, N-4-methylphenyl benzamide and N,N-dibenzoyl-4-methyl aniline. When the same reaction is carried out in protic solvents, the formation of benzil, N-4-methylphenyl benzamide, N,N-dibenzoyl-4-methyl aniline and benzoic acid is observed. The characterization uses spectral data and comparison (undepressed mixed melting point and identical IR spectra) with authentic samples. This study derives an interesting route for photooxidative fragmentation of oxazoline-2-one ring systems. The proposed mechanism involves the dioxetane derivative which after fragmentation yields radicals to afford aforementioned products.
Key words: Irradiation, column, chromatographic separation, evaporation, solvents.
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