Cyclisation of 2-azidodiphenylmethane and 2-azidobiphenyls by regiospecific N-attack of arylnitrenium–aluminium chloride complexes

H Takeuchi, M Maeda, M Mitani…

Index: Takeuchi, Hiroshi; Maeda, Munenori; Mitani, Michiharu; Koyama, Kikuhiko Journal of the Chemical Society, Chemical Communications, 1985 , # 5 p. 287 - 289

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Abstract

Decomposition of 2-azidodiphenylmethane and 2-azidobiphenyls in CH2C12 in the presence of AICI3 gave 9,lO-dihydroacridine and carbazoles, respectively, in reasonable yields by regiospecific N-attack of an arylnitrenium-AICI3 complex. ... We have reported that a phenylnitrenium ion generated from phenyl azide in the presence of trifluoroacetic acid (TFA) or trifluoromethanesulphonic acid (TFSA) brings about an aromatic N-substitution. 1~ Thus, we expected that the decom- ...