The reaction of tetralones and their enamines with cyanogen halides: a new synthesis of 2-naphthylamines

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Abstract
2-Tetralones and their enamines have been aromatised by cyanogen bromide to the corresponding naphthols and naphthylamines. Under similar conditions, 1-tetralone gave 2-bromo-1-tetralone. Cyanogen chloride cyanated 2-tetralone enamines in the 1-position, but did not affect 1-(3,4-dihydro-1-naphthyl)pyrrolidine (a 1-tetralone enamine). P.m.r. and i.r. data show that 2-cyano-1-tetralone exists as the ketone, whereas 1-cyano-2-tetralone is almost entirely enolic.

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