Hydrolysis of Esters and Amides in Strongly Basic Solution. Evidence for the Intermediacy of Carbanions
Kinetic studies of the decomposition of the carbaninons derived from a number of esters and amides of p-nitrophenylacetic acid in strongly basic solution have been carried out.Kinetic solvents isotop effects and the large Hammett ρ value for substituents on the aromatic ring of substituted phenyl esters of p-nitrophenylacetic acid suggest decomposition occurs by an E1cB mechanism.Furthermore, it appears that the carbanion can decompose by either an ionic or a free-radical mechanism, depeneding on the nucleofugality of the leaving group.An intermediate predicted to be 4-nitrophenyl ketone ha been detected spestroscopically in a number of cases.
Broxton Trevor, J.,Duddy, Neil W.
p. 1186 - 1191
(2007/10/02)
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