Oxidative transformation of tert-cyclobutanols by palladium catalysis under oxygen atmosphere.

doi:10.1021/JO0016475

Paper

Oxidative transformation of tert-cyclobutanols by palladium catalysis under oxygen atmosphere.

Published Jan 23, 2001 · T. Nishimura, K. Ohe, S. Uemura

The Journal of organic chemistry

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Abstract

Palladium(II)-catalyzed oxidative reaction of tert-cyclobutanols involving the cleavage of a C-C bond via beta-carbon elimination under atmospheric pressure of oxygen is described. An alkylpalladium intermediate produced by beta-carbon elimination from a Pd(II) alcoholate gives a variety of products, depending on the substituents on the cyclobutane ring, in which reactions such as dehydrogenative ring opening, ring expansion and ring contraction are involved. For some substrates, the addition of a catalytic amount of ethyl acrylate dramatically accelerates the reaction. In all cases, the dehydrogenative products are obtained and the Pd(II)-hydride species produced at the final stage can be converted again to active Pd(II) species by molecular oxygen.

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Study Snapshot

Palladium(II)-catalyzed oxidative transformation of tert-cyclobutanols under oxygen atmosphere produces various dehydrogenative products, with ethyl acrylate catalytically accelerating the reaction for some substrates.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Oxidative transformation of tert-cyclobutanols by palladium catalysis under oxygen atmosphere.

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References

Citations

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Pd-catalyzed ring-opening polymerization of cyclobutanols through C(sp3)-C(sp3) bond cleavage produces novel polyketone materials with unique substitution patterns.

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