Elbs persulfate oxidation

[1] The reaction is generally performed in water at room temperatures or below, using equimolar quantities of reagents.

[2][3][4] The reaction is disadvantaged by moderate to low chemical yields with recovery of starting material and complete consumption of the persulfate.

Despite this, the Elbs reaction remains generally useful in a research setting, as it is simple to perform and is tolerant of a wide range of other functional groups, which are not oxidised under these conditions.

[4] A reaction mechanism has been postulated which accounts for the observed para substitution featuring the tautomeric para carbanion of the starting phenolate ion:[5] It begins with nucleophilic displacement on the peroxide oxygen of the peroxodisulfate (peroxydisulfate) ion, to give an intermediate sulfate group (3), which is then hydrolyzed to the hydroxyl group.

Add the following: E. J. Behrman, The Elbs & Boyland-Sims Oxidations: An Updated Literature Survey.