6533b7d0fe1ef96bd125b945
RESEARCH PRODUCT
A Convenient Generation of Acetic Acid Dianion
Salvador GilMargarita ParraEnrique Sotocasubject
DiethylamineNucleophilic additionOrganic Chemistrychemistry.chemical_elementGeneral MedicineMedicinal chemistryAcetic acidchemistry.chemical_compoundchemistryAldol reactionOrganic chemistryLithiumPhysical and Theoretical ChemistryCarbaniondescription
The lithium enediolate of acetic acid can be generated efficiently, as a 0.5 M solution in THF, using lithium amides prepared from n-butyllithium in THF and either diethylamine or 1,3,3-trimethyl-6-azabicyclo-(3.2.1)-octane (AZA). Its reaction with carbonyl compounds leads to the corresponding β-hydroxy acids in good to moderate yields. Better yields are usually obtained when these amines are added in sub-stoichiometric amounts. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-08-05 | European Journal of Organic Chemistry |