Mechanism of the palladium-catalyzed intramolecular hydroalkylation of 7-octene-2,4-dione.

doi:10.1021/JA0293002

Paper

Mechanism of the palladium-catalyzed intramolecular hydroalkylation of 7-octene-2,4-dione.

Published Jan 30, 2003 · Hua Qian, R. Widenhoefer

Journal of the American Chemical Society

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62

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Abstract

Cyclization of (E)-7,8-dideuterio-7-octene-2,4-dione [(E)-1-7,8-d(2)] catalyzed by PdCl(2)(CH(3)CN)(2) (2) formed cis-2-acyl-3,4-dideuteriocyclohexanone (cis-3-3,4-d(2)) in 64% yield as the exclusive isotopomer. This experiment, in conjunction with additional deuterium labeling experiments, was in accord with a mechanism for the conversion of 1 to 3 catalyzed by 2 involving attack of the enol carbon atom on a palladium-complexed olefin followed by palladium migration and protonolysis from a palladium enolate complex.

Study Snapshot

Palladium-catalyzed intramolecular hydroalkylation of 7-octene-2,4-dione produces cis-3-3,4-dideuteriocyclohexanone in 64% yield, supporting a mechanism for the conversion of 1 to 3 involving attack of

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Mechanism of the palladium-catalyzed intramolecular hydroalkylation of 7-octene-2,4-dione.

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