- Boyland-Sims oxidation
The Boyland-Sims oxidation is the
chemical reaction ofaniline s with alkalinepotassium persulfate , which afterhydrolysis forms "ortho"-hydroxyl anilines.Ref|Boyland1953Ref|Boyland1954Ref|Behrman1988The "ortho"-isomer is formed predominantly. However, the "para"-sulfate is formed in small amounts with certain anilines.Ref|Boyland1956
Reaction mechanism
Behrman has shown that the first intermediate in the Boyland-Sims oxidation is the formation of an arylhydroxylamine-O-sulfate (2).Ref|Behrman1992 Rearrangement of this
zwitterion ic intermediate forms both the ortho- and para-amino aryl sulfates (3a and 3b).References
# Boyland, E. "et al." "
J. Chem. Soc. " 1953, 3623.
# Boyland, E.; Sims, P. "J. Chem. Soc. " 1954, 980.
# Behrman, E. J. "Org. React." 1988, "35", 421-511. (Review)
# Boyland, E.; Sims, P.; Williams, D. C. "Biochem. J." 1956, "62", 546.
# Behrman, E. J. "J. Org. Chem. " 1992, "57", 2266. (DOI|10.1021/jo00034a016)ee also
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Elbs persulfate oxidation
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