A Synthon Approach to Selective Fluorination Using Vinyl- and Propargylphosphonates

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The focus of this research involves the development of second generation fluorophosphonate synthons. To this end, the synthesis of fluorinated gamma-silyl-alpha-fluoroalkyne phosphonates in conjunction with solid phase fluorination studies, the use of phosphonate as a leaving group and the synthesis of cyclic alpha-fluoro- and alpha, alpha-difluoroalkyne phosphonates will be carried out. The long-term goals of the research include solid phase fluorine incorporation of a gem-difluoropropargyl unit, synthesis of fluorinated phosphonic analogs of nucleotides, synthesis of heterocyclic alpha-fluoro phosphonates and transmission of chirality at the fluoromethylene carbon in alpha-fluorpropargyl phosphonates. With this renewal Research in Undergraduate Institutions (RUI) award, the Synthetic Organic Program is supporting the research of Dr. Gerald B. Hammond of the Department of Chemistry at the University of Massachusetts, Dartmouth. Professor Hammond will focus his work on developing a group of reagents known as fluorophosphonate synthons. These molecules are versatile synthetic intermediates as precursors to fluorophosphonates , an important group of biological phosphate mimics, and as fluorine containing synthons for the preparation of organofluoro compounds. The proposed research will be carried out, in the main, by undergraduate students.