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The Lead Tetraacetate Oxidation of Δ6-Unsaturated Tertiary Alcohols. Eight-Membered Cyclic Ether Formation

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In the lead tetraacetate oxidation of the unsaturated tertiary cyclic alcohols la and 1b, and the acyclic alcohol 15a, all possessing a Δ6olefinic bond ( with respect to the hydroxyl group), the α-acetoxylated eight-membered cyclic ethers 6a, 6b and 16a, respectively, were obtained. With these substrates lead tetraacetate reacts at the double bond and, if at all, only by weak association with the hydroxyl group, so that fragmentation products derived from alkoxy radical intermediates (such as 2) were not formed. The mechanism of this cyclisation reaction is discussed.

Affiliations: 1: Department of Chemistry, Faculty of Science, University of Belgrade Studenski trg 16, P.O. Box 550, YU-11001 Belgrade, and Institute of Chemistry, Technology and Metallurgy Belgrade, Yugoslavia


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