Abstract
AbstractDeprotonation 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.
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