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Paper | Special issue | Vol 67, No. 1, 2006, pp.233-246
Published online, 26th August, 2005
DOI: 10.3987/COM-05-S(T)19
Coupling of Fischer Carbene Complexes with Alkynylstyrene Oxides: Synthesis of Benzoxepinones in Competition with Internal Oxygen Atom Transfer

Lei Zhang and James W. Herndon*

*Department of Chemistry & Biochemistry, New Mexico State University, P. O. Box 30001, Las Cruces, NM 88003-2505, U.S.A.

Abstract

The coupling of Fischer carbene complexes with conjugated enyne epoxides has been examined. The reaction proceeds by carbene-alkyne coupling to afford an epoxyvinylcarbene complex, which then undergoes CO insertion and cyclization to afford a benzoxepinone or intramolecular oxygen atom transfer to afford a dienone derivative.