Synthesis of Carbazoles from N-(N, N-Diarylamino) phthalimides with Aluminum Chloride via Diarylnitrenium Ions

Y Kikugawa, Y Aoki, T Sakamoto

Index: Aoki, Yutaka; Saito, Yuko; Sakamoto, Takeshi; Kikugawa, Yasuo Synthetic Communications, 2000 , vol. 30, # 1 p. 131 - 140

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Citation Number: 34

Abstract

Treatment of N-(N,N-diphenylamino)phthalimide (1a) with AlCl 3 (5 mol equiv) in benzene for 4 h at room temperature gave carbazole (81%) along with N-p-biphenyl-N-phenylamine (11%), which indicates that AlCl 3 -mediated heterolytic cleavage of the N−N bond produces