Abstract
The reaction of N-(sulfonyloxy) amides with bases proceeds by initial formation of an α-lactam intermediate. A primary kinetic deuterium isotope effect, k H /k D =2.17. a leaving group effect. β 1g CH3 =0.50, and nucleophilic trapping all confirm that the α-lactam is produced in the rate-determining step. Ring opening to an ion pair and nucleophilic addition to C-2 produce 2-substituted amide products
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