RUI: Electrophilic Reactions of Fluorosubstituted Alkenes with Chlorosulfonyl Isocyanate and some other Electrophiles

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With this Renewal Award, the Chemical Structure, Dynamics, and Mechanisms Program continues to support Professor Dale F. Shellhamer of Point Loma Nazarene College in his investigations of electrophilic reactions of fluorosubstituted alkenes. These studies will be focused on the mechanism of the reaction of chlorosulfonyl isocyanate with monofluoroalkenes to generate fluoro substituted beta-lactams. Kinetic measurements, product studies and computational chemistry will be employed to gain an understanding of the factors that cause additions of chlorosulfonyl isocyanate to change from an apparent one-step process with most fluoroalkenes to a step-wise process with hydrocarbons and some fluorocarbon alkenes. Although non-fluorinated lactams and other fluorinated compounds are often important pharmaceutical agents, fluorinated lactams are largely unexplored and should prove to be very interesting medicinal compounds.An important aspect of this project will be the involvement of undergraduate students as researchers in all facets of the project. Students will gain expertise in organic synthesis, NMR spectroscopy, mass spectrometry, vibrational spectroscopy and computational chemistry. Professor Shellhamer has an excellent record of involving undergraduates in research and inspiring them to go on to advanced study in chemistry and medicine.