The reaction is relevant as a tool in organic synthesis and is a key step in the biosynthesis of prostaglandins.
In the reaction mechanism for this organic reaction the base abstracts the acidic α-proton of the peroxide 1 to form the carbanion 4 as a reactive intermediate which rearranges to the ketone 2 with expulsion of the hydroxyl anion 3'.
An alternative reaction mechanism involving direct nucleophilic displacement on the peroxide link of the amine followed by an elimination reaction is considered unlikely based on the outcome of this model reaction:[2] The peroxide 1 converts to the hydroxyketone 2 by action of triethylamine but the alternative route through hydroxylamine 3 by nucleophilic displacement with Lithium diisopropylamide and the ammonium salt 4 (by methylation with methyl trifluoromethanesulfonate) fails.
Not only alkoxides but any leaving group capable of carrying a negative charge will do for instance nitrate esters R–C(R)(H)–O–NO2.
The original 1951 publication concerned the conversion of potassium t-butyl peroxide and 1-phenylethyl bromide to ultimately acetophenone and t-butanol with piperidine as the base: