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]

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The ortho-isomer is formed predominantly. However, the para-sulfate is formed in small amounts with certain anilines.^[4]

Reaction mechanism

Behrman has shown that the first intermediate in the Boyland-Sims oxidation is the formation of an arylhydroxylamine-O-sulfate (2).^[5] Rearrangement of this zwitterionic intermediate forms both the ortho- and para-amino aryl sulfates (3a and 3b).

References

1. ^  Boyland, E. et al. J. Chem. Soc. 1953, 3623.
2. ^  Boyland, E.; Sims, P. J. Chem. Soc. 1954, 980.
3. ^  Behrman, E. J. Org. React. 1988, 35, 421-511. (Review)
4. ^  Boyland, E.; Sims, P.; Williams, D. C. Biochem. J. 1956, 62, 546.
5. ^  Behrman, E. J. J. Org. Chem. 1992, 57, 2266. (doi:10.1021/jo00034a016)

See also

• Elbs persulfate oxidation