After the starting material in this reaction is deprotonated, it reacts with the halogen to form an N-haloamide.
After the starting material in this reaction is deprotonated, it reacts with the halogen to form an N-haloamide. This intermediate is itself deprotonated, leading to a migration of the R group from carbon to nitrogen , causing the halogen to leave and producing an unstable compound also seen in similar reactions by Lossen, Schmidt, and Curtius. That compound, an isocyanate, dissociates to form carbon dioxide and the final product. A different reaction sometimes called exhaustive methylation that involves the conversion of a quaternary ammonium salt to an alkene and an amide was also described by this reaction's namesake. For 10 points, name this reaction that converts a primary amide to a primary amine that has one fewer carbon.
After the starting material in this reaction is deprotonated, it reacts with the halogen to form an N-haloamide.
Hofmann rearrangement [or Hofmann degradation; prompt on Hofmann; do not accept "Hofmann elimination"]