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RESEARCH PRODUCT
Configuration of Enolates of β-Ketocarboxylic Acid Esters — Carbocation-Carbanion Salts
Herbert MeierMartin AdamMonika Bußsubject
chemistry.chemical_classificationChemistryOrganic ChemistrySalt (chemistry)General ChemistryNuclear magnetic resonance spectroscopyCarbocationAlkali metalMedicinal chemistryMethanechemistry.chemical_compoundDeprotonationOrganic chemistryPhysical and Theoretical ChemistryX ray analysisCarbaniondescription
Deprotonation of (Z)- or (E)-3-hydroxy-2,3-dimesitylpropenoic acid methyl ester (1a) with tetrakis(dimethylamino)-methane (3) led to stable salt (E)-2a, which belongs to a very rare species of salts that consist of a heteroatom-stabilized carbocation and a heteroatom-stabilized carbanion. An analogous guanidinium salt (E)-2b was formed in the reaction of 3-oxo-2,3-diphenylpropanoic acid methyl ester (1b) and 3. The molecular structures of these enolates were studied by NMR spectroscopy and an X-ray analysis of (E)-2a {MC[N(CH3)2]3} and compared with those of the corresponding alkali enolates.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1996-12-01 | Liebigs Annalen |