Abstract
The lack of reactivity of
N
-(α-ethoxycarbonylalkyl)-2,4,6-tri-substituted pyridinium salts toward nucleophilic displacement of the
N
-substituent is ascribed to stereoelectronic effects. Although such esters undergo ready base hydrolysis to give the corresponding acids, they are highly resistant to attack by other nucleophiles at the C&z.dbd6;O function; this behaviour is rationalised.