Fission of Activated Carbon—Nitrogen and Carbon—Sulphur Bonds. I. Polarographic Reduction of the Single C—N-Bond

Abstract

In methoiodides of α-aminoketones and in aminoaldehydes with the grouping-COCH₂-NR₃ ⁽⁺⁾ or -COCH=CH-NR₃ ⁽⁺⁾ the C-N⁽⁺⁾-bond is reduced. The products of the two-electron reduction of α-aminoketones are the ketone -COCH₃ and the amine NR₃.When the carbonyl compound is reducible (as it is in the case of acetophenone formed in the reduction of ω-piperidinoacetophenone methoiodide (I) and hydrochloride (II) or phenacylpyridinium chloride (VII) or in the case of acrolein formed in the reduction of β-N-triethylaminoacrolein perchlorate (VII)), another two-electron step, corresponding to the reduction of a ketone formed in the first step, appears. In hydrochlorides of α-aminoketones the C-N⁽⁺⁾ bond is reduced in the protonized form only, with the grouping -COCH₂NHR₂ ⁽⁺⁾ but not in the free base. A comparison with other reductions of single bonds is given.