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

…, JR Lafrance, P Demerseman

Index: Martin, Robert; Lafrance, Jean Ronald; Demerseman, Pierre Bulletin des Societes Chimiques Belges, 1991 , vol. 100, # 7 p. 539 - 548

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Citation Number: 9

Abstract

Abstract 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.