Reactions of nitrones with sodium iodide-trifluoroacetic anhydride system. Comments on the Beckmann rearrangement of aldonitrones and competitive processes of nucleophilic addition

Abstract The systematic studies of the reaction of aldonitrones with the NaI-TFAA system were performed. The reaction engaged was recognised as a previously known process called ‘the Beckmann rearrangement of nitrones’. Some mechanistic considerations on this transformation and competitive nucleophilic additions are presented in order to explain the origin of iodine release and its observed stoichiometry as well as of some products isolation. The intermediacy of C - and N -iodo species (including iodonium cations) in the presence of iodide anions, is postulated.