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A New Twist on Amide Solvolysis
Author(s) -
Aubé Jeffrey
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201108173
Subject(s) - solvolysis , amide , substituent , chemistry , twist , oxazoline , stereochemistry , hydrolysis , medicinal chemistry , organic chemistry , catalysis , geometry , mathematics
Planar but destabilized : Amides prepared from hindered amines and carbonyl compounds containing an electron‐withdrawing substituent (EWG) have recently been shown to undergo solvolysis at greatly enhanced rates under neutral conditions. The key is increased access to a twisted amide conformation that undergoes a proton switch, ultimately leading to the observed products.