The Boyland–Sims oxidation is the

chemical reaction A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the pos ...

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...

s with alkaline

potassium persulfate Potassium persulfate is the inorganic compound with the formula K2 S2O8. Also known as potassium peroxydisulfate, it is a white solid that is sparingly soluble in cold water, but dissolves better in warm water. This salt is a powerful oxidant, c ...

, which after

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

forms ''ortho''-hydroxyl anilines. The reaction is generally performed in water at room temperatures or below, using equimolar quantities of reagents. The ''ortho''-isomer is formed predominantly. However, the ''para''-sulfate is formed in small amounts with certain anilines.

Scope and mechanism

The reaction is disadvantaged by moderate to low

chemical yield In chemistry, yield, also referred to as reaction yield, is a measure of the quantity of moles of a product formed in relation to the reactant consumed, obtained in a chemical reaction, usually expressed as a percentage. Yield is one of the pr ...

s, but is simple to perform and uses mild conditions. Some competitive oxidation of the nitrogen has been observed. Behrman has shown that the first intermediate in the Boyland–Sims oxidation is the formation of an arylhydroxylamine-O-sulfate (2). Rearrangement of this

zwitterion In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively- and negatively-charged functional groups. : With amino acids, for example, in solution a chemical equilibrium wil ...

ic intermediate forms the

ortho- Ortho- is a Greek prefix meaning “straight”, “upright”, “right” or “correct”. Ortho may refer to: * Ortho, Belgium, a village in the Belgian province of Luxembourg In science * arene substitution patterns, two substituents that ...

sulfate (5), which then hydrolyses to form the ortho-hydroxyl aniline. Boyland-Sims-Oxidation

Scope and mechanism

See also

References

Further reading