PHENOXENIUM IONS. IDENTICAL INTERMEDIATES IN THE ACID-CATALYZED SOLVOLYSIS OF N-TOSYL-O-ARYLHYDROXYLAMINES AND IN THE THERMOLYSIS OF N-ARYLOXYPYRIDINIUM SALTS

Article abstract of DOI:10.1016/S0040-4020(01)91336-5

The acid-catalyzed solvolysis of N-tosyl-O-arylhydroxylamines in aromatic solvents and the thermolysis of N-aryloxypyridinium salts involve common intermediates, phenoxenium ions, for the formation of hydroxybiphenyl derivatives.Diphenylethers are formed when the heterolysis of the N-O bonds is slow and the aromatic solvent has high nucleophilicity.