α‐Bromonitroalkanes could engage amines in amide bond formation with the assistance of
N
‐iodosuccinimide. Evidence collected during the initial study, and consistent with subsequent mechanistic studies, suggested that the key carbon‐nitrogen bond‐forming step involved a nucleophilic nitonate carbon and an electrophilic iodamine nitrogen. This inversion of polarity relative to all other known amide bond‐forming reactions led to the description of this reaction as Umpolung Amide Synthesis (UmAS).
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