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Communication | Regular issue | Vol 12, No. 2, 1979, pp.217-225
Published online, 1st January, 1970
DOI: 10.3987/R-1979-02-0217
Photocyclization and Photooxygenation of 1,3,4,5-Tetraarylimidazolin-2-ones

Otohiko Tsuge,* Koji Oe, and Hisataka Inoue

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


Irradiation of 1,3,4,5-tetraarylimidazolin-2-ones in benzene, under nitrogen, with or without iodine gave the corresponding phenanthroimidazolinones. In the presence of oxygen, however, the imidazolinone was photochemically converted to the corresponding benzanilide, N-benzoyl-N ,N’-diphenylbenzamidine and p-benzoylphenyl isocyanate, besides the phenanthroimidazolinone. On the other hand, the dye-sensitized photooxygenation afforded the benzanilide, amidine, N,N’-dibenzoyl-N,N’-diphenylurea, and/or 1,4-diaza-1,3-butadiene derivative, whose yields depended on the nature of substituents of the imidazolinone and of the solvent employed. Mechanistic consideration of the photooxygenation was also described.