Perkow reaction

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.

[3] When the substituent is n-butyl the reaction product is the classical Perkow adduct.

When the substituent on the other hand is phenyl (not shown) the phosphite has a preference for reaction with the acyl group leading to an ethyl enol ether.

Key in explaining the difference in reactivity is the electron density on the α-keto carbon atom.

90%) in the Perkow reaction can be used as phosphorylating reagents, e.g. able to transform AMP into ATP.