| PREPARATION |
First isolable, covalent selenium azide A stable organoselenium compound containing a covalently bound azido group has been isolated and characterized by chemistry professor Thomas M. Klapötke, research scientist Burkhard Krumm, and crystallographer Kurt Polborn of the University of Munich, in Germany [J. Am. Chem. Soc., 126, 710 (2004)]. Klapötke's group has prepared and studied a number of main-group azides over the years, including ionic selenonium azides of the type R3SeN3. The Munich researchers also have been intrigued by published reports on the in situ organoselenium reagent C6H5SeN3, which has been reported to add azidoselenenyl groups to double bonds, although it's too unstable to be isolated or fully characterized. These developments led them to synthesize the selenenyl azide shown (red = Se, blue = N) by substituting the chlorine atom of 2-(CH3)2NCH2C6H4SeCl with an azido group using NaN3 or AgN3. Spectroscopic data and the X-ray crystal structure, supported by the calculated structure, indicate that the amino nitrogen coordinates to selenium, forming a heterocyclic zwitterion with an unusual three-atom, four-electron NSeN bond system. The selenenyl azide is "an attractive candidate" for applications in organic synthesis, they add. |
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