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

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

  • 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



  1. J. Chem. Soc. Chem. Comm. J. Grimshaw;A.P. De Silva
  2. J. Org. Chem. v.30 D. Elad;D.U. Rao;U.I. Stenberg
  3. Can. J. Chem. v.53 D.J. Carlsson;L.H. Gan;D.M. Wiles
  4. Org. chemic v.12 Beilsteiv
  5. Org. chemic v.12 Beilsteiv
  6. Org. chemic v.12 Beilsteiv
  7. Org. chemic v.12 Beilsteiv
  8. Org. chemic v.12 Beilsteiv
  9. Org. chemic v.14 Beilsteiv
  10. Chemical Review v.78 J.D. Coyle
  11. J. Korean Chem. Socc. v.29 Y.T. Park;S-R Do;K-D. Lee
  12. Org. chemic v.12 Beilsteiv