A Facile and Efficient Method for the Rearrangement of Aryl-substituted Epoxides to Aldehydes and Ketones using Bismuth Triflate

Ram S. Mohan, Kaushik A. Bhatia, Kyle J. Eash, Nicholas M. Leonard, Matthew C. Oswald

Research output: Journal ArticleArticlepeer-review


<div class="line" id="line-15"> Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01&ndash;0.1 mol% Bi(OTf)3&bull;xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C&horbar;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&bull;Et2O, currently used to effect epoxide rearrangements.</div>
Original languageAmerican English
JournalTetrahedron Letters
StatePublished - 2001


  • Bismuth and compounds
  • epoxides
  • rearrangements.


  • Organic Chemistry

Cite this