Boyland–Sims oxidation

The Boyland–Sims oxidation is the chemical reaction of anilines with alkaline potassium persulfate, which after hydrolysis forms ortho-hydroxyl anilines.

[1][2][3] The reaction is generally performed in water at room temperatures or below, using equimolar quantities of reagents.

However, the para-sulfate is formed in small amounts with certain anilines.

[4] The reaction is disadvantaged by moderate to low chemical yields, but is simple to perform and uses mild conditions.

[3] Behrman has shown that the first intermediate in the Boyland–Sims oxidation is the formation of an arylhydroxylamine-O-sulfate (2).