RUI: Electrophilic Reactions of Fluorosubstituted Alkenes- Predicting Regiochemical Product Distributions

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This award to Professor Dale F. Shellhamer of the Chemistry Department at Point Loma Nazarene College in San Diego, CA has as its goal the understanding of the influence that vinyl fluorine atoms have on the product regiochemistry from electrophilic reactions with halogens, interhalogens, and open-ion electrophiles like triflic acid and chlorosulfonyl isocyanate. This is important since it is known that fluorine, more than any other element, has the ability to completely alter product regiochemistry for electrophilic reactions. In addition to the experimental studies, quantum chemical computational studies will be employed to predict and verify the anticipated drastic changes that fluorine atoms have on product distributions. Further, the proposed study with chlorosulfonyl isocyanate will provide a new class of fluoro beta-lactams, an important study since beta-lactam functionality is present in several classes of antibiotics. Further, studies of fluorine containing compounds are important since a large number of agrochemicals and pharmaceuticals contain fluorine atoms.Among the most important broader impacts of this research is the mentoring of undergraduate researchers and training them as future scientists in a predominantly undergraduate institution. Prof. Shellhamer and Point Loma Nazarene College are exemplary in this regard and they have an excellent record of their undergraduate research participants obtaining advanced degrees in science and medicine. They also have an excellent record of participation by minority and women students and it is expected that this will continue. Further, as mentioned above, because fluorine is found in many pharmaceuticals and agrochemicals, understanding the chemistry of fluorine will help in the design of new generations of these substances.