Mechanism
The rearrangement takes place via SN2 reaction (Scheme 8).
Scheme 6
For Related Reactions on Phosphonate Ester Synthesis, see:
Michaelis-Becker Reaction
Hydrogen phophonate reacts with alkyl halide in the presence of base to give an alkyl phosphonate. However, the yield is often lower than the corresponding Michaelis-Arbuzov reaction.
Mechanism
Kabachnik-Fields Reaction
The three-component coupling of a carbonyl compound, an amine and a hydrogen phosphonate leads to α-aminophosphonates. This has been an important method in drug discovery research for generating peptidomimetic compounds.
The Photo-Arbuzov Reaction
Irradiation of benzyl phosphate leads to rearrangement to give benzyl phosphonate.
Examples:
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