Acid Catalyzed Ring Opening Reaction of trans-Stilbene Oxide

The acid catalyzed ring opening of trans-stilbene oxide was investigated in DMSO, DMF, THF, and dioxane and the products, meso and dl-hydrobenzoins and diphenylacetaldehyde, were determined. In the solvents of high polarity, inversion of configuration was observed in most products, and the opposite was true in the solvents of low polarity. There was no direct relation between rearrangement products and polarity of solvents.