Acid-catalyzed hydrolysis of diethyl .alpha.-arylvinyl phosphates

Frampton, Roger; Tidwell, Thomas T.; Young, Virginia A.

doi:10.1021/ja00759a038

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Cited by 6 publications

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The stereoselective synthesis of ?-haloenol phosphates?A reinvestigation of the reaction of ?-haloketones with diethyl phosphite

Ding

Huang

1999

Heteroatom Chem.

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A new pathway for the reaction involving an α‐haloketone and a dialkyl phosphite has been suggested, It offers a highly stereoselective synthetic procedure leading to β‐haloenol phosphates in one‐pot reactions that take place in good yields. However, normal Pudovik reaction products were formed when the reaction was carried out using a relatively small amount of base. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 55–59, 1999

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The stereoselective synthesis of ?-haloenol phosphates?A reinvestigation of the reaction of ?-haloketones with diethyl phosphite

Ding

Huang

1999

Heteroatom Chem.

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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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