Photochemistry of Benzanilides (II). Photo-Fries Type Reaction of Benzanilides

벤즈아닐리드류의 광화학 (제2보). 벤즈아닐리드류의 Photo-Fries 형 반응

  • Yong-Tae Park (Department of Chemistry, Kyungpook National University) ;
  • Han-Chun Yun (Department of Chemistry, Kyungpook National University) ;
  • Sang-Rok Do (Department of Chemistry, Kyungpook National University) ;
  • Young-Du Kim (Department of Industrial Chemistry, Keimyung Junior College)
  • 박용태 (경북대학교 자연과학대학 화학과) ;
  • 윤한춘 (경북대학교 자연과학대학 화학과) ;
  • 도상록 (경북대학교 자연과학대학 화학과) ;
  • 김영두 (계명대학교 실업전문대학 식품가공학과)
  • Published : 1985.08.20


Several benzanilides were prepared by acylation of anilines with substituted benzoyl chlorides. While 2-chlorobenzanilides were photocyclized, 2-methylbenzanilide and 2'-methylbenzanilide were cleaved to give photo-Fries type products. 2-Nitrobenzanilide and 2'-nitrobenzanilide were inert in the above conditions due to lowering energy of the excited state by the nitro group. N, N-dibenzoylaniline and N, N-di-(2-chlorobenzoyl) aniline gave photo-Fries type reaction products effectively. In the benzanilide photo-Fries type reaction the excited singlet state was believed to be involved, since no oxygen effect was observed on the reaction rate. Quantum yield for 2-methylbenzanilide is higher in nonpolar and less viscous solvents than in polar and viscous solvents. The solvent cage radical pair is suggested in the photo-Fries type reaction of benzanilides.



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