The effect of fluorine substitution on radical, diradical, carbanion, carbene, and pericyclic reactions will be conducted. By strategic placement of fluorine on a substrate, the kinetic, stereochemical, and regiochemical effects will be evaluated. Processes to be investigated include Cope rearrangements, electrocyclic reactions, cyclopropane and vinylcyclopropane rearrangements, and methylcyclopropane and methylcyclobutane rearrangements. A highlight of the investigation will be the use of intramolecular cyclization reactions to examine steric, polar, and stereoelectronic reactivity effects of fluorine substituents on reactions of radicals, carbanions, carbenes, and 1,3-dipoles. %%% This grant from the Organic Dynamics Program supports the studies of Professor W. R. Dolbier at the University of Florida on fluorocarbon chemistry. The incorporation of fluorine into a variety of substances can enhance their utility and provide materials with superior properties for use in a variety of different applications ranging from chemically resistant fibers to polymers which resist penetration of water in high humidity environments. In order to maximize the impact of fluorine on the substrate to which it is attached, it is necessary to fully understand the effect that fluorine has on chemical reactions under a variety of different conditions. The studies of Professor Dolbier will provide invaluable information which will help accelerate the development of fluorine based materials and insure that full advantage is taken of the unique properties of fluorocarbons.
