The Development and Characterization of Radical Anion Clock Reactions

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With support from the Organic Dynamics Program, Dr. Tanko will examine the mechanism of decay of several cyclopropyl ketyl anions. In particular, questions that surround one potential mode of decomposition, i.e., a mechanism that proceeds via rapid and irreversible cyclopropane ring opening, will be addressed in this study. The potential use of these radical anion systems as "clocks" to measure the rates of competing bimolecular processes will be explored. Finally, potential applications of radical anions reactions to organic synthesis will be studied. %%% Single electron transfer (SET) provides an important reaction pathway in organic chemistry. The species that are produced via SET processes are called "radical anions". Their intermediacy in such reactions can be inferred by the appearance of rearranged products. Dr. Tanko has devised methodology for studying radical anion intermediates and for utilizing these intermediates as mechanistic probes to obtain detailed information about the mechanisms of competing reactions. In addition to their inherent mechanistic interest, radical anion reactions can be used to promote reactions that are likely to be useful for synthesizing structural units of important natural products.