A facile and efficient method for the rearrangement of aryl-substituted epoxides to aldehydes and ketones using bismuth triflate

Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01 0.1 mol% Bi(OTf)(3). xH(2)O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C-O 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. Et2O, currently used to effect epoxide rearrangements. (C) 2001 Elsevier Science Ltd. All rights reserved.