Synthesis and Chemistry of Bridgehead Alkenes

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This research program of Dr. Kenneth J. Shea will be supported by the Organic Synthesis Program in the Department of Chemistry at the University of California at Irvine. The principal investigator will investigate the chemical and physical properties of the carbon-carbon double bond, the so-called olefinic group, under structural conditions that will distort the unsaturated linkage under geometrically controlled, well defined conditions. The changes in properties will be utilized to develop new methods of synthesizing complex structures. The carbon-carbon double bond is perhaps the most ubiquitous functional group in organic chemistry. The chemical and spectroscopic properties of this functional group may be significantly modified by twisting the double bond out of coplanarity. This project involves the synthesis of molecules that contain twisted carbon-carbon double bonds. The synthetic effort makes available molecules that permit study of how the chemical and spectroscopic properties of carbon-carbon double bonds respond to twisting. One particularly interesting prospect is to identify reaction manifolds that may be particularly sensitive to specific molecular deformations. It is also the intention to utilize molecules with twisted double bonds as key intermediates in the synthesis of stereochemically complex natural products.