Oxidative Rearrangement via 1,2-Aryl Migration using Hydroxy(tosyloxy)iodobenzene in a Polar Aprotic Solvent

A series of geminal beta,beta-ditosyloxy ketones were synthesized in moderate to good yields through hydroxy(tosyloxy)iodobenzene-mediated ditosyloxylation of readily accessible alpha,beta-unsaturated ketones in a polar aprotic solvent. A mechanism has been proposed for the synthesis of the geminal beta,beta-ditosyloxy ketones, and entails an oxidative rearrangement involving a 1,2-aryl migration.