BoylandâSims oxidation | |
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Named after | Eric Boyland Peter Sims |
Reaction type | Organic redox reaction |
Identifiers | |
RSC ontology ID | RXNO:0000181 |
The BoylandâSims oxidation is the chemical reaction of anilines with alkaline potassium persulfate, which after hydrolysis forms ortho-hydroxyl anilines. [1] [2] [3] 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. [4]
The reaction is disadvantaged by moderate to low chemical yields, but is simple to perform and uses mild conditions. Some competitive oxidation of the nitrogen has been observed. [3]
Behrman has shown that the first intermediate in the BoylandâSims oxidation is the formation of an arylhydroxylamine-O-sulfate (2). [5] Rearrangement of this zwitterionic intermediate forms the ortho- sulfate (5), which then hydrolyses to form the ortho-hydroxyl aniline.