RUI: gamma-C-Alkylation of 1,3-Dicarbonyl Compounds using Equilibrating Conditions

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professors Brad Andersh and Wayne Bosma of Bradley University will use a tandem approach of synthesis and computational chemistry to investigate the mechanism and the scope and limitations of gamma-carbon-alkylation reactions of 1,3-dicarbonyl compounds using equilibrating bases such as carbonates and alkoxides. The specific mechanistic questions that will be addressed are: (1) why gamma-alkylation rather than alpha-alkylation occurs when an equilibrating base is used and (2) how the gamma-anion of a 1,3-dicarbonyl compound forms. The development of chemical processes that are cost-effective and environmentally safe is an area of emphasis in the chemical community. The goal of the proposed research is to understand and exploit a new method for selectively modifying organic compounds at one or more similar sites. The proposed methodology is procedurally less complex than existing methods and will allow for new greener chemical processes. The broader impacts of the project include (1) providing scientists with a greater understanding of this green method, and (2) the training of future scientists by providing research opportunities for undergraduate and high school students.