Volume 19, Issue 2
Preparative Organic Chemistry
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ChemInform Abstract: Cycloaddition of the Trimethylenemethane-Palladium Complex to Activated Six-Membered and Medium-Size Ring Enones.

D. G. CLEARY

D. G. CLEARY

Evans Chem. Lab., Ohio State Univ., Columbus, OH 43210, USA

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L. A. PAQUETTE

L. A. PAQUETTE

Evans Chem. Lab., Ohio State Univ., Columbus, OH 43210, USA

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First published: January 12, 1988

Abstract

The cyclohexenones (I) react with the acetoxymethylallylsilane (II) in the presence of a Pd(0) catalyst generated in situ to produce the methylenecyclopentanocyclohexanones (III).

ChemInform Abstract

The cyclohexenones (I) react with the acetoxymethylallylsilane (II) in the presence of a Pd(0) catalyst generated in situ to produce the methylenecyclopentanocyclohexanones (III). The methyl-substituted compounds (IIIa) and (IIIc) are only formed in moderate yields in contrast to the corresponding methoxycarbonyl derivatives (IIIb) and (IIId). The cyclooctenonecarboxylate (IV) is converted to thebicyclic methylene ketone (V) in an analogous manner.

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