Control of the ‘extended’E1cB mechanism of acyl group transfer in activated esters of acrylic acids
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 2,p. 131-133
- https://doi.org/10.1039/p29830000131
Abstract
Aminolysis and alkaline hydrolysis of aryl propenoates are shown to proceed via a normal nucleophilic substitution mechanism. The ‘extended’E1cB mechanism of hydrolysis involving attack of hydroxide ion at the β carbon followed by expulsion of the phenolate ion from the resulting carbanion is shown not to occur with the parent propenoate. The ‘extended’E1cB mechanism is taken by the hydrolysis of 2-cyano-3-(4-methoxyphenyl)propenoate esters due to the stabilising effect of the cyano-group on the intermediate carbanion.Keywords
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