The oxazolinone intermediate in the hydrolysis and aminolysis of N-benzoylglycine derivatives
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 9,p. 947-953
- https://doi.org/10.1039/p29750000947
Abstract
The Brønsted type relationship with the pKa of the departing hydroxy-group for the alkaline hydrolysis (kOH) of N-benzoylglycine esters exhibits a break consistent with a change in mechanism. Substituted phenyl esters hydrolyse via an oxazolinone intermediate and the high Brønsted selectivity indicates a rate-determining step with considerable C–OAr bond cleavage in its transition state. The formation of the intermediate occurs via a pathway where ionisation of the N-benzoylglycine NH, intramolecular attack, and decomposition of the tetrahedral intermediate are discrete steps. Aminolysis proceeds largely through the ester rather than via the oxazolinone intermediate.Keywords
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