Journal
TETRAHEDRON LETTERS
Volume 42, Issue 46, Pages 8129-8132Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(01)01519-2
Keywords
bismuth and compounds; epoxides; rearrangements
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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.
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