Reactions of 1-alkoxycarbonylpyridinium salts with nucleophiles: stereoelectronic restrictions on carbonyl activation of α-nucleophilic attack
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2365-2368
- https://doi.org/10.1039/p19820002365
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 CO function; this behaviour is rationalised.Keywords
This publication has 0 references indexed in Scilit: