Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 66, Issue 4, Pages 1455-1465Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0016475
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Palladium(II)-catalyzed oxidative reaction of tert-cyclobutanols involving the cleavage of a C-C bond via P-carbon elimination under atmospheric pressure of oxygen is described. An alkylpalladium intermediate produced by P-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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