Hofmann-Type Rearrangement of Imides by in Situ Generation of Imide-Hypervalent Iodines(III) from Iodoarenes

The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from Phl, m-CPBA, and TsOH center dot H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted by the formation of an imide-lambda(3)-iodane intermediate.