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.
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