Interaction of N, N-dimethylperfluoroarylamines with nitric and nitrous acids

Abstract

N, N-Dimethylpentafluoroaniline enters easily into reactions with a mixture of nitric and sulphuric acids or nitric acid with conversion of the side chain. In the reactions with mixtures of HNO 3 and H 2SO 4, the formation of N-nitroso- N-methyl and N-nitro- N-methylpentafluoroanilines is observed. The ratio of these products was found to depend on the ratio of the acids: the formation of N-nitro- N-methylpentafluoroaniline increases with the quantity of sulphuric acid; N-nitroso- N-methylpentafluoroaniline is obtained when only nitric acid is employed. N, N-Dimethylperfluoro- p-toluidine, N, N-dimethylperfluoro-2,4-xylidine, N, N-dimethylperfluoro-5-aminoindane undergo similar transformations. N-Nitroso derivatives were converted by a mixture of HNO 3 and H 2SO 4, HNO 3 or NO 2BF 4 into the corresponding N-nitro derivatives. Formation of the corresponding N-nitroso- N-methyl derivatives occurs when N, N-dimethylpentafluoroaniline, N, N-dimethylperfluoro- p-toluidine are treated with HNO 2.