Synthesis of phenoxyamines

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/sub a/ of the phenol in a manner explainable in terms of a competing bimolecular decomposition reaction involving the 2,4-dinitrophenoxyamine. By use of an appropriately substituted phenol, this phenomenon can be exploited to give high yields of phenoxyamines having oxygenated substitution patterns that were unattainable by previous methods.