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Paper | Special issue | Vol 84, No. 1, 2012, pp. 625 - 635
Published online: 12th July, 2011
DOI: 10.3987/COM-11-S(P)35
Unusual Base-Induced Rearrangement of exo-9-Oxabicyclo[4.2.1]non-7-ene Oxide to exo-8-Hydroxybicyclo[3.3.0]octan-2-one

David M. Hodgson,* Matthew A. H. Stent, Robert S. Paton, and Francis X. Wilson

*Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.

Abstract

Reaction of exo-9-oxabicyclo[4.2.1]non-7-ene oxide with n-BuLi gives exo-8-hydroxybicyclo[3.3.0]octan-2-one. Potential reaction pathways for this unusual rearrangement were evaluated with the aid of computational studies. The process is proposed to proceed by elimination to a transient allene oxide, which rearranges to a trans-epoxide enolate before undergoing epoxide α-lithiation and transannular CH insertion.

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