Preparation and biological activity of the isomers of dimethyl-1,3-dicarbomethoxy-1-propen-2-yl phosphate (Bomyl)

Newallis, Peter E.; Lombardo, Pasquale; Gilbert, Everett E.; Spencer, Elvins Y.; Morello, Antonio

doi:10.1021/jf60153a031

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2010

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Perkow Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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The preparation of vinyl (or enol) phosphates from α‐halo carbonyl compounds and trivalent phosphorus reagents and is generally known as the Perkow reaction. The study finds that, α‐halo aldehydes are more reactive than α‐halo ketones; whereas α‐halo esters are the least reactive species for the Perkow reaction, and α‐halo amides do not react at all. It has been found that the more α‐halo atoms in the carbonyl compound, the faster the reaction occurs. All the suitable reagents have been suggested for this reaction Both the electronic character of phosphorus and the steric effects are prominent in the Perkow reaction, as indicated by the predominant trans ‐configuration in vinyl phosphates. It is observed that the course of the reaction depends on the nature and position of halogen on the carbonyl compounds as well as the reaction temperature. This reaction has importance for the preparation of vinyl phosphates.

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