ORGN 139 |
| Due to frequent occurrence of nitrogen atoms in the structures of biologically active compounds, chemoselective functionalization of organic molecules with nitrogen-containing groups is among the most important goals in modern organic synthesis. Our group recently reported electrochemical aziridination of olefins and imination of sulfoxides with N-aminophtalimide. Of particular current interest are a-bromoaziridines, available via direct aziridination of a-brominated olefins. The chemistry a-haloaziridines has not been extensively studied due to their instability. Herein we present our investigations of the mechanism of the rearrangement of a-bromoaziridines into a-bromohydrazones (Scheme 1). The reaction is believed to occur through concerted heterolytic fission. Our results suggest that the nature of substituent at nitrogen is the determining factor in this chemistry. Synthetic application of a-bromohydrazones and a-bromoaziridines will be presented.
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Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster
Division of Organic Chemistry |
