Boyland-Sims Oxidation

E. Boyland et al., J. Chem. Soc. 1953, 3623; E. Boyland, P. Sims, ibid. 1954, 980.

Alkaline persulfate oxidation of aromatic amines to yield predominantly the o-amino aryl sulfates. Acid-catalyzed hydrolysis generates the o-hydroxy aryl amines:

Regioselectivity/mechanistic study: E. J. Behrman, J. Org. Chem. 57, 2266 (1992). Review: idem, Org. React. 35, 421-511 (1988). Cf. Elbs Persulfate Oxidation.