The formation of N-methylbenzanilide in the decomposition of 2-(N-methyl-N-phenylcarbamoyl) benzenediazonium fluoroborate in acetic acid

Abstract

The decomposition of 2-(N-methyl-N-phenylcarbamoyl) benzenediazonium fluoroborate (2) in acetic [²H] acid gives a monodeuterio-N-methylbenzanilide. This and other evidence indicates that the N-methylbenzanilide produced in the title reaction is not formed by hydrogen atom abstraction from the solvent. An alternative mechanism involving acetolysis of an arylcopper intermediate is suggested.