Synthesis of Some Substituted Pyrroline-1-Oxides by Catalytic Hydrogenation of Aliphatic Gamma-Nitrocarbonyi Compounds

Abstract

Various pyrroline-1-oxides were prepared by the catalytic hydrogenation of appropriately substituted gamma-nitrocarbonyl compounds. Initially the reaction affords a mixture of the nitrone and the corresponding hydroxylamine, but copper(II)-catalyzed aerial oxidation readily converts the hydroxylamine to the desired cyclic nitrone. This method was found to be more convenient than the zine-ammonium chloride reduction and the corresponding yields were comparable.