N-Demethylation of N,N-dimethylanilines by the benzotriazole N-oxyl radical: evidence for a two-step electron transfer-proton transfer mechanism

The reaction of the benzotriazole N-oxyl radical (BTNO) with a series of 4-X-N,N-dimethylanilines (X = CN, C[F.sub.3], C[O.sub.2]C[H.sub.2]C[H.sub.3], C[H.sub.3], O[C.sub.6][H.sub.5], OC[H.sub.3]) is examined in C[H.sub.3]CN. The results are interpreted based on the electron-transfer mechanism from the N,N-dimethylanilines to the BTNO radical followed by deprotonation of the anilinium radical cation (ET-PT mechanism).