Intermediates formed by anodic oxidation of N-acetyl-epsilon-amino-caproicacid

Anodic oxidation of N-acetyl-epsilon-aminocaproic acid was performed in CH3 ONa/CH3OH in conditions which favoured either one- or two-electron oxidatio n. Products distribution was analysed by GC-MS and confirmed by H-1-NMR. Th e study focuses on the stabilization routes of the intermediate carbenium i on, resulted by two-electron anodic oxidation. It has beeen found that a la rge number of metoxyderivative isomers and alkene isomers are formed. This shows that the carbocation initially generated on the electrode isomerises immediately, before reacting with the solvent. Other reaction products iden tified in this experiment have been assigned to a reaction mechanism which involves the presence of the carbocation in the double layer. The heterogen eous generation of carbocations (at the electrode/solution interface) deter mines the distribution of products. One-electron oxidation leads especially to the dimer that can be obtained by this method. Electrode nature is deci sive in the orientation of the reaction towards one- or two-electron oxidat ion route.