Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01-0.1 mol% Bi(OTf)3,xH20. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic (-0 bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3' Et20, currently used to effect epoxide rearrangements.

A Facile and Efficient Method for the Rearrangement of Aryl-Substituted Epoxides to Aldehydes and Ketones Using Bismuth Triflate.-The title reaction is regioselective with aryl-substituted epoxides and the products arise from cleavage of the benzylic C-O bond. -(BHATIA, KAUSHIK A.; EASH, KYLE J.; LEONARD, NICHOLAS M.; OSWALD, MATTHEW C.; MOHAN, RAM S.; Tetrahedron Lett. 42 (2001) 46, 8129-8132; Dep. Chem., Ill. Wesleyan Univ., Bloomington, IL 61701, USA; EN)