Boyland–Sims oxidation


The Boyland–Sims oxidation is the chemical reaction of anilines with alkaline potassium persulfate, which after hydrolysis forms ortho-hydroxyl anilines.
The ortho-isomer is formed predominantly. However, the para-sulfate is formed in small amounts with certain anilines.

Reaction mechanism

Behrman has shown that the first intermediate in the Boyland–Sims oxidation is the formation of an arylhydroxylamine-O-sulfate. Rearrangement of this zwitterionic intermediate forms the ortho- sulfate, which then hydrolyses to form the ortho-hydroxyl aniline.