RUI: Electrophilic vs Free Radical Reactions of Halogen Systems with Terminal Perfluoroalkenes and Their Derivatives

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With this Research in Undergraduate Institutions (RUI) award, the Organic Dynamics Program supports the research of Dr. Dale F. Shellhamer of the Department of Chemistry at Point Loma Nazarene College. Professor Shellhamer explores the reaction conditions required to cause an ionic reaction of halogens, interhalogens and other halogen systems with various unreactive terminal perfluoroalkenes. A thorough understanding of addition reactions to perfluoroalkenes and perfluorohydrocarbons alkenes is necessary for the development of new polymerization processes and synthesis of new monomers.This study is designed to supply data that will provide a thorough understanding of halonium ions derived from a variety of substituted terminal perfluoroalkenes. The relative symmetry of the halonium ions in a series of substituted perfluoroalkenes will be compared to related data reported for halonium ions of analogous hydrocarbons.The applications of fluoropolymers cover broad areas such as: water, fuel and oil repellency, thermal stability, resistance to chemicals, UV radiation and weathering, and lubricants with a low coeffficient of friction retaining high thermal stability. The advantages of those materials offset the disadvantage of high unit cost. The research is designed to enhance the understanding of the reactions of fundamental fluorine chemistry which should have applications in many commercial processes. This project is well suited for undergraduates. They will carry out syntheses and use modern instruments to characterize a large number of compounds generated from this study. Students are encouraged to suggest mechanistic interpretations of the experimental data and to propose control experiments to confirm an ionic pathway and ensure that kinetic products are being reported. The undergraduate research program at Point Loma Nazarene College also serves as a recruitment tool for outstanding high school students interested in various branches of science.