Bismuth(III) Oxide Perchlorate Promoted Rearrangement of Epoxides to Aldehydes and Ketones

Ram S. Mohan, Andrew M. Anderson, Jesse M. Blazek, Parie Garg, Brian J. Payne

Research output: Journal ArticleArticlepeer-review


<div class="line" id="line-15"> Aryl-substituted epoxides and aliphatic epoxides with a tertiary epoxide carbon undergo smooth rearrangement in the presence of 10&ndash;50 mol% bismuth(III) oxide perchlorate, BiOClO4&bull;xH2O, to give carbonyl compounds. The rearrangement is regioselective with aryl substituted epoxides and a single carbonyl compound arising from cleavage of benzylic C&horbar;O bond is formed. BiOClO4&bull;xH2O is relatively non-toxic, insensitive to air and inexpensive, making this catalyst an attractive alternative to more corrosive and toxic Lewis acids such as BF3&bull;Et2O or InCl3 currently used to effect epoxide rearrangements.</div>
Original languageAmerican English
JournalTetrahedron Letters
StatePublished - 2000


  • Organic Chemistry

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