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

✍ Scribed by Kaushik A Bhatia; Kyle J Eash; Nicholas M Leonard; Matthew C Oswald; Ram S Mohan

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 125 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01519-2

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✦ Synopsis

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 BF 3 •Et 2 O, currently used to effect epoxide rearrangements.

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