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Palladium-Catalyzed Isomerization of Methylenecyclopropanes in Acetic Acid

Min Shi,* Bao-Yu Wang and Jin-Wen Huang

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Email: mshipub.sioc.ac.cn

M. Shi, B.-Y. Wang, J.-W. Huang, J. Org. Chem., 2005, 70, 5606-5610.

DOI: 10.1021/jo050560m (free Supporting Information)


Abstract

Pd(PPh3)4-catalyzed isomerization of methylenecyclopropanes (MCPs) proceeds smoothly at 80C in acetic acid and toluene to give 1-substituted or 1,1-disubstituted dienes in good to excellent yields. The mechanism is discussed.

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proposed mechanism



Key Words

Dienes, Isomerizations


ID: J42-Y2005-800