Intramolecular Anodic Olefin Coupling Reactions

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This research addresses the development of new approaches to carbon-carbon bond formation by oxidation of functionalized dienes using electrochemistry. Preliminary results indicate that five, six and seven-membered rings can be formed in high yield by this methodology. The studies involve the design, synthesis and electrochemical oxidation of a series of coupling substrates aimed at probing the overall requirements of the reaction. These experiments are designed to examine the coupling reactions involving the initiating and terminating groups that are compatible with the reaction conditions, the size of the rings that can be formed, the effect of substituents, the stereochemistry of the products, and the effect of the reaction conditions on product formation. Finally, the project examines the synthetic utility of the reactions for constructing polycyclic ring systems and initiating tandem cyclization reactions. %%% With this award, the Synthetic Organic Program of the Chemistry Division will support the research of Dr. Kevin D. Moeller of the Department of Chemistry at Washington University. The project is in the general area of synthetic methodology and focusses on the development of carbon-carbon bond formation by oxidation of functionalized dienes using electrochemical methods. These types of reactions are extremely important because they allow the development of entirely new routes for molecular synthesis. Oxidative organic electrochemistry is ideally suited for initiating the key step in these reactions since it can selectively generate reactive intermediates under neutral conditions.