Mechanism of autoreduction of 2,2,6,6-tetramethyl-1,4-dioxopiperidinium cation in alkaline medium

Autoreduction of 2,2,6,6-tetramethyl-1,4-dioxopiperidinium ion to nitroxyl radical in alkaline medium involves a number of parallel and consecutive reactions. The primary products of the reaction of 2,2,6,6-tetramethyl-1,4-dioxopiperidinium with hydroxide ion are three nitroso compounds and N -hydroxy-2,2,6,6-tetramethylpiperidine N -oxide. Isomerization of the nitroso compounds and elimination of acetone from the N -oxide give cyclic hydroxylamines which reduce the initial cation to nitroxyl radical, being oxidized to nitrones.