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 (2). Rearrangement of this zwitterionic intermediate forms both the ortho- and para-amino aryl sulfates (3a and 3b).