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Treatment of 2-(perfluoroalkyl)aniline with 2-tolylmagnesium bromide or chloride or their substituted analogs yields an acridine containing a shorter perfluoroalkyl group at the 9 position and devoid of the methyl group of the Grignard substrate. Interestingly, no acridine is produced in an attempted reaction with aryl magnesium bromide without the ortho methyl group. With 2-fluoro-6-methylphenylmagnesium bromide the methyl group is eliminated and the fluorine is retained in the acridine product. Results of the mechanistic studies strongly suggest that loss of the methyl group occurs as methanol during air oxidation and hydrolysis of the intermediate products during aqueous workup.

heterocyclic communications

Synthesis of 9-(C n-1 F 2n-1 )-substituted acridine by the reaction of 2-(C n F 2n+1 )-substituted aniline with  ortho -methyl-substituted aromatic Grignard reagent