Basic bromination of this functional group produces an isocyanate that reacts with water to form carbamic acid that rapidly decarboxylates.
The "most twisted" example of this functional group has increased reactivity due to its bridgehead position. Competition from hydrogen bonding severely slows a reaction that forms an alpha-acyloxy example of this functional group, providing evidence against an ionic mechanism in favor of the concerted addition of a ketone, carboxylic acid and isocyanide. This functional group and an alkene make up a Michael acceptor that is (*) cross-linked in SDS-PAGE gel. Basic bromination of this functional group produces an isocyanate that reacts with water to form carbamic acid that rapidly decarboxylates. The Passerini reaction forms this functional group, which is hydrolyzed more slowly than an ester and found in the side chain of asparagine. For 10 points, name this functional group that undergoes the Hofmann rearrangement and is found in peptide bonds.
The "most twisted" example of this functional group has increased reactivity due to its bridgehead position.
amides [accept: carboxamides; accept: lactams; accept aza-2-cycloalkanones; accept alpha-acyloxy-(beta-diketo)-amides; do not accept "amines"]