Conversion of aryl-N-sulphohydroxylamines (N-aryl-N-hydroxysulphamic acids) to o-aminoaryl hydrogen sulphates by acetone, and related reactions

Abstract

The potassium salt of 2-naphthyl-N-sulphohydroxylamine and potassium phenyl-N-sulphohydroxylamine are converted into 2-amino-1-naphthyl hydrogen sulphate and o-aminophenyl hydrogen sulphate respectively at room temperature in acetone. The 2-naphthylhydroxylamine derivative requires light or pyridine to effect the change, the phenylhydroxylamine derivative rearranges spontaneously. Treatment of the two arylhydroxylamines with pyridine–sulphur trioxide in acetone also gives the o-aminoaryl sulphates. The involvement of carbonyl compounds in these and other reactions and their possible relevance to the metabolism of aromatic amines is discussed.