Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 23, Pages 8740-8747Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo061238u
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The decatungstate W10O324- homogeneous photocatalyzed oxygenation of tetrasubstituted alkenes has been mechanistically studied. In all cases, allylic hydroperoxides are the major products. The primary inter- and intramolecular as well as the remote delta-secondary deuterium kinetic isotope effects for the photooxidation of the 2,3-dimethyl-2-butene and 1,1,1-trideuterio-7-methyl-2-(trideuteriomethyl)octa-2,6-diene along with product analysis suggest a hydrogen abstraction in the rate-determining step. For comparison, singlet oxygen photosensitized oxidations of the above substrates were also studied.
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