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Perkow reaction
The Perkow reaction is an organic reaction in which a trialkyl phosphite ester reacts with a haloketone to form a dialkyl vinyl phosphate and an alkyl halide.
In the related Michaelis–Arbuzov reaction the same reactants are known to form a beta-keto phosphonate which is an important reagent in the Horner–Wadsworth–Emmons reaction on the road to alkenes. The Perkow reaction, in this respect is considered a side-reaction.
== Reaction mechanism ==
The reaction mechanism of the Perkow reaction consists of a nucleophilic addition of the phosphite at the carbonyl carbon forming a zwitterionic intermediate. The zwitterionic intermediate rearranges to a cationic species while eliminating the halide. The cationic species then dealkylates through a second nucleophilic displacement in which the halide anion attacks one of the phosphite alkoxide substituents forming an enol phosphate.〔Organophosphorus chemistry. XVII. Kinetics and mechanism of the Perkow reaction''
Irving J. Borowitz , Steven Firstenberg , Grace B. Borowitz , David Schuessler J. Am. Chem. Soc.; 1972; 94 pp 1623–28; 〕
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