The focus of this research is the synthesis of of an array of fully fluorinated compounds having skeletons with four to twelve carbon atoms. Representative molecules contain conjugated pi-electron systems and polycyclic skeletons composed of small strained rings. Studies of the compounds will include determination of product composition, kinetic and thermodynamic measurements and quantum mechanical calculations. Comparison of the fluorocarbons with their hydrocarbon counterparts will shed light on the nature of fluorine as a substituent in organic chemistry. %%% With this award, the Synthetic Organic Program is supporting the research of Dr. David M. Lemal of the Department of Chemistry at Dartmouth College. Professor Lemal will focus his work on gaining insight into the nature and chemistry of fluorocarbons.