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A Facile and Efficient Method for the Rearrangement of Aryl-substituted Epoxides to Aldehydes and Ketones using Bismuth Triflate
Tetrahedron Letters (2001)
  • Ram S. Mohan, Illinois Wesleyan University
  • Kaushik A. Bhatia
  • Kyle J. Eash
  • Nicholas M. Leonard
  • Matthew C. Oswald
Abstract

Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01–0.1 mol% Bi(OTf)3•xH2O. 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.

Keywords
  • Bismuth and compounds,
  • epoxides,
  • rearrangements.
Disciplines
Publication Date
2001
Citation Information
Ram S. Mohan, Kaushik A. Bhatia, Kyle J. Eash, Nicholas M. Leonard, et al.. "A Facile and Efficient Method for the Rearrangement of Aryl-substituted Epoxides to Aldehydes and Ketones using Bismuth Triflate" Tetrahedron Letters Vol. 42 (2001)
Available at: http://works.bepress.com/ram_mohan/15/