A Reexamination of the Retro‐fries Rearrangement of Some o‐Hydroxyketones

The retro-Fries rearrangement, catalyzed by protic and Lewis acids, was studied for some o-hydroxyketones. The results are consistent with the mechanism of an heterolytic cleavage and rearrangement. It appears that, in general, Lewis acids do not induce the retro-Fries rearrangement of o-hydroxyketones. However, in certain cases, it may be brought about by the presence of a protic acid generated in situ, from a solvent-catalyst interaction.