Efficient intramolecular general acid catalysis of vinyl ether hydrolysis by the neighbouring carboxylic acid group

AJ Kirby, NH Williams

Index: Kirby, Anthony J.; Williams, Nicholas H. Journal of the Chemical Society, Chemical Communications, 1991 , # 22 p. 1643 - 1644

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Citation Number: 34

Abstract

Intramolecular catalysis by the C02H group of the hydrolysis of €-I -methoxy-2-(2-carboxypheny1 )ethylene 5, shows an effective molarity of almost 300 M, the highest measured for intramolecular proton transfer to carbon. ... Intramolecular general acid-base catalysis is an intrinsically inefficient process, with measured effective molarities (EM) rarely exceeding 10 ~ . 1 A striking exception is intramolecular general acid catalysis of the hydrolysis of salicylic acid derivatives such ...

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