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KMID : 1059519850290040441
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Journal of the Korean Chemical Society
1985 Volume.29 No. 4 p.441 ~ p.447
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Photochemistry of Benzanilides (II). Photo-Fries Type Reaction of Benzanilides
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Park Yong-Tae
Yun Han-Chun
Do Sang-Rok
Kim Young-Du
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Abstract
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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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