ISSN:
0947-3440
Keywords:
3-Oxocarboxylic acid esters
;
Enolates
;
Configuration, influence of the counter ions
;
Guanidinium salts
;
X-ray analysis
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 {M=C[N(CH3)2]3} and compared with those of the corresponding alkali enolates.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961227