Nitrones and oxaziridines. XXII. Preparation and cyclization of some δ,ε-unsaturated hydroxylamines

Abstract

Four δ,ε-unsaturated hydroxylamines have been prepared by reduction of the related oximes by sodium cyanoborohydride. Only two of these-those containing terminal olefinic groups-undergo spontaneous cyclization to N-hydroxypyrrolidines, which can be oxidized easily to 1-pyrroline 1-oxides. The acyclic and cyclic hydroxylamines have been characterized by their products of reaction with phenyl isocyanate.