Synthesis of Phenoxyamines

Article abstract of DOI:10.1021/jo00182a007

Treatment of phenols with 2,4-dinitrophenoxyamine leads to the synthesis of phenoxyamines through an amine exchange reaction.Yields for this reaction are sensitive to the pK_a of the phenol in a manner explainable in terms of a competing bimolecular decomposition reaction involving the 2,4-dinitrophenoxyamines.By use of an appropriately sustituted phenol, this phenomenon can be exploited to give high yields of phenoxyamines having oxygenated substitution patterns that were unattainable by previous methods.