The Development of New Radical Processes

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This project will explore the synthetic potential of several important radical processes: the fragmentation of cyclopropyl and cyclobutylcarbinyl radicals; the generation, inversion and cyclization of dioxolanyl, oxiranyl, and aziridinyl radicals. These latter functionalized radicals can be generated from readily available chiral precursors that will lead to enantiomerically pure compounds. Dioxolanyl, oxiranyl, and aziridinyl radicals have not been the subject of extensive study and in the case of the latter two, all but ignored as potential chiral reactants in chemical synthesis. In addition to the synthetic potential of these processes, interesting mechanistic questions have also been posed. The success of these studies will provide new avenues of synthesis that may be applicable to the preparation of important antibiotics through pathways inaccessible by anionic and cationic methods. Modern methods of chemical analysis, i.e., nuclear magnetic resonance and mass spectroscopy, will be used in the identification of the new materials prepared in this work. %%% With this award, the Organic Synthesis Program will support the research of Dr. Frederick E. Ziegler at Yale University. The research explores new synthetic methodology based on free radical based reactions that could replace the more well developed anionic and cationic based methodology.