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Paper | Regular issue | Vol 43, No. 3, 1996, pp.633-640
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7340
Reaction of 1-Hydroxyphthalimide Derivatives with Aluminum Chloride in Benzene

Kensaku Uto, Takeshi Sakamoto, Keita Matsumoto, and Yasuo Kikugawa*

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-02, Japan


The reaction of 1-hydroxyphthalimide derivatives with AlCl3 in benzene has been investigated. From 1-hydroxyphthalimide (1a) 2-hydroxy-3,3-diphenyl-2,3-dihydroisoindol-1-one (2) and 1,1-diphenyl-1H-benzo[d][1,2]oxazine-4-one (3) are obtained by initial attack of benzene on the imide carbonyl, assisted by the neighboring oxygen atom. Heating 2 with Lewis acid (AlCl3) in benzene results in ring expansion to afford 3, while heating 3 with protic acid (H2SO4) leads to ring contraction to give 2. From O-(2-phenethyl)- and O-benzoyl derivatives (1b and c), 1,2-diphenylethane (4) and benzophenone (5) are obtained, respectively, by the heterolytic cleavage of an C-O bond.