Enol-Keto Tautomerism of α -ketophosphonates

Enol-Keto Tautomerism of α -ketophosphonates

A number of α -ketophosphonates have been prepared and their enol-keto tautomerism has been studied by means of proton and phosphorus NMR and infrared spectroscopy and the ferric chloride test. Aliphatic ketophosphonates exist largely in the keto tautomeric forms, with only a small amount of enol fo...

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Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS Vol. 78; no. 6; pp. 3301 - 3304
Main Authors: Tam, Coretta C., Mattocks, Karen L., Tishler, Max
Format: Journal Article
Language:English
Published: United States National Academy of Sciences of the United States of America 01-06-1981
National Acad Sciences
Subjects:
Carbenes
Chemical equilibrium
Chlorides
Ethers
Line spectra
Liquids
Phosphonic acids
Phosphorus
Physical Sciences: Chemistry
Protons
Tautomers
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Summary:A number of α -ketophosphonates have been prepared and their enol-keto tautomerism has been studied by means of proton and phosphorus NMR and infrared spectroscopy and the ferric chloride test. Aliphatic ketophosphonates exist largely in the keto tautomeric forms, with only a small amount of enol forms present. All the aromatic acylphosphonates studied, however, enolize extensively. An x-ray analysis confirmed enolization and E configuration as the only stereochemical isomer. Reaction of diazomethane with diethyl p-methoxyphenylacetyl phosphonate gave a mixture of O-methylation and carbene insertion products, whereas the same reaction with diethyl isobutyryl phosphonate gave only carbene insertion products.
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ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.78.6.3301