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DOI: 10.1055/sos-SD-031-01513

Rück-Braun, K.; Priewisch, B.Science of Synthesis, (2007311340.

Peroxymonosulfuric acid (H2SO5, Caro's Acid) oxidizes primary arylamines 59 to the corresponding nitrosoarenes 60 (Scheme 31).[‌71‌‌76‌] The active oxidant is the peroxymonosulfate ion (HSO5). Solutions of Caro's acid are prepared from the corresponding sodium or ammonium peroxodisulfates and sulfuric acid prior to use; the amount of active oxygen available being determined by iodometric titration.[‌77‌] The oxidation is often carried out in slightly acidic aqueous solution (pH36.5), the pH being adjusted by addition of sodium or potassium carbonate.[‌71‌,‌78‌] The main byproducts are the corresponding diaryldiazene oxides. In many cases separation of the volatile nitroso compounds can be achieved by steam-distillation.

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