Nitriles electrooxidation

Indirect electrooxidation of cyclic aziridines using NaCl or NaBr as a redox catalyst results in C(l)-C(2) bond cleavage under formation of the corresponding keto nitriles. This reaction is explained by the intermediate generation of an azaallenyl cation, which is hydrated to the o -hydroxyimine. Further oxidation by Cl" then would lead to the open-chain keto A-chloroimine, which by HCl elimination forms the keto nitrile, while its hydrolysis leads to the keto aldehyde as a side product [32] ... 

In the case of branched C-terminal amino acids, methoxylation at the C-terminus is accompanied by formation of imidazolidine-4-ones by cx-oxidation at the C-terminus followed by intramolecular attack of the nitrogen of the N-terminal amino acid. Tliis reaction can be performed in high yields, if the electrooxidation is performed in aceto-nitrile/5% methanol [200]. 

Kimura and coworkers [378] have also reported that electrooxidative desulfenylation of Michael-type thiol adducts of a, jS-unsaturated esters, ketones, and also nitriles resulted in the formation of E- and Z-olefins as major products, respectively ... 

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