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Paper | Regular issue | Vol 48, No. 12, 1998, pp.2593-2600
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8357
Reaction of N-Phenoxyphthalimide Derivatives with Aluminum Chloride in Benzene

Kensaku Uto, Etsuko Miyazawa, Katsuhiro Ito, Takeshi Sakamoto, and Yasuo Kikugawa*

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japana


N-Phenoxyphthalimides react with AlCl3 in benzene to form products of intramolecular N-C and intramolecular C-C bond formation via aryloxenium ion intermediates. N-Phenoxy derivatives having an electron-withdrawing substituent on the para position react with solvent benzene on the imide carbonyl, assisted by the neighboring oxygen atom, to produce N-(4-substituted phenoxy)-3,3-diphenyl-2,3-dihydroisoindol-1-ones.