Mechanisms of Endocyclic Atom Transfers

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With this renewal award the Organic and macromolecular Chemistry Program supports the work of Dr. Peter Beak in the Department of Chemistry at the University of Illinois at Urbana-Champaign. The research aims to extend the earlier work on endocyclic atom transfer reactions to include transfers of fluorine, chlorine, bromine, oxygen, and sulfur. Methods to be used include: 1) following kinetics of the reactions with double labelling, 2) NMR spin saturation transfer, 3) competitive intramolecular transfers, and 4) the formation of transient double labelled species and surrogate intermolecular reporter molecules.It is anticipated that the information obtained in the proposed studies will increase our understanding of the reaction profiles involved in atom transfer reactions, will be of theoretical interest, and will have practical consequences for synthesis, especially in making optically active compounds useful for pharmaceuticals. Graduate students involved in the work will gain valuable experience in organic synthesis, product characterization, and kinetics and mechanism, currently in great demand in the pharmaceutical industry.