With this award, the Organic Dynamics Program will support the research of Dr. Philip E. Eaton of the Department of Chemistry at the University of Chicago. Dr. Eaton is recognized for his syntheses of molecules containing special geometries that force the constituent carbons to rehybridize and adopt unusual bonding parameters. These properties produce systems which provide new insights about the role of bonding in chemical reactivity. Current studies are focused on the synthesis of hexaprismane, 1,3-dehydrocubane, pentaprismane, azahomocubanone, azacubane and other highly strained molecules. These compounds will be characterized fully by spectroscopy and by their reaction chemistry. The dehydrocubanes will be studied in detail using spectroscopic methods to measure the energy difference between a very highly twisted olefin and its carbene isomer. The cubyl carbocation is being investigated in order to determine what factors make this structure more readily accessible than originally predicted.