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The reaction between a stable nitroxide, 2, 2, 6, 6-tetramethyl-4-chloropiperidinyl-1-oxy, la and aromatic amines and heterocycles, 3—9, in methylene chloride in the presence of trifluoroacetic acid, has been investigated. The corresponding radical cations of the amines and the heterocycles were readily generated by this reaction, which could persist for a long period of time in the system. Kinetic ESR studies were performed to elucidate the reaction mechanism and the results showed that the formation of the radical cations involves one-electron transfer reaction between the active oxidant, the oxoammonium trifluoroacetare, 2a, which results from the disproportionation of the nitroxide in the presence of trifluoroacetic acid, and the substrates studied. This affords a facile method for the generation of radical cations from aromatic amines and heterocyclics by the action of an organic oxidant.
The reaction between a stable nitroxide, 2, 2, 6, 6-tetramethyl-4-chloropiperidinyl-1-oxy, la and aromatic amines and heterocycles, 3-9, in methylene chloride in the presence of trifluoroacetic acid, has been investigated. The corresponding radical cations of the amines and the heterocycles were formed well by this reaction, which could persist for a long period of time in the system. Kinetic ESR studies were performed to elucidate the reaction mechanism and the results showed that the formation of the radical cations involves one-electron transfer reaction between the active oxidant, the oxoammonium trifluoroacetare, 2a, which results from the disproportionation of the nitroxide in the presence of trifluoroacetic acid, and the substrates studied. This affords a facile method for the generation of radical cations from aromatic amines and heterocyclics by the action of an organic oxidant.