 | ||
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 (2). Rearrangement of this zwitterionic intermediate forms the ortho- sulfate (5), which then hydrolyses to form the ortho-hydroxyl aniline.
References
Boyland–Sims oxidation Wikipedia(Text) CC BY-SA