Novel Methods for Regioselective Vinylic and Aromatic Fluorination

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This project addresses the development of a novel method for vinylic fluorination via the Julia olefination. Sulfides derived from 2-mercapto-1,3-benzothiazole will be used to mediate the alpha introduction of fluorine at the stage of the sulfide, sulfoxide, or sulfone. Terminal alpha-fluorobenzothiazolosulfones derived from these products will be condensed with aldehydes to yield fluoro olefins. Unsymmetrical 1,2-diaryl ethylenes containing a regioselectively placed vinyl fluorine will be synthesized, then photocyclized to aryl systems containing embedded phenanthrenoid moieties. Additional functional group handles will allow for the elaboration of the fluoroaromatics to putative metabolites. The chemistry that will be developed will also be applied in conjunction with ring-closing metathesis reactions for the synthesis of regioselectively fluorinated cyclic olefins.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Barbara Zajc of the Chemistry Department at CUNY City College. While organic compounds containing fluorine atoms have a multitude of applications ranging from therapeutics, to entities useful for metabolic studies to NMR probes, introduction of fluorine into organic molecules continues to represent a formidable task. Professor Zajc and her students are developing new methods for the selective synthesis of fluorinated organic compounds and the putative products of their metabolism. Such compounds offer promise in a variety of applications, including the analysis of the factors responsible for the carcinogenicity of polycyclic aromatic hydrocarbons. These studies will be carried out by a diverse group of undergraduate and graduate students at CUNY City College.