Subject neighbouring group effects

Amide hydrolysis is not only subject to acid and base catalysis, but may be also brought about by a neighbouring group in the amide, the so-called propinquity catalysis effect. Wolfrom et a/.238 were among the first to suggest this possibility, in order to explain the observed hydrolysis of aldonamides, viz. 

Secondary deuterium isotope effects are important in the study of neighbouring-group participation in solvolytic reactions.61 This subject has now been reviewed at considerable length. Other evidence bearing on participation is also discussed. 

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