ORGN 468 |
| Nitrotriazoles are energetic materials. Normally they are difficult to prepare. Here we report the first preparation of nitrotriazoles from the reaction of nitroacetylene (HCCNO2) and azido compounds (RN3) via 1,3-dipolar cycloaddition. Nitroacetylene is, believably, the most electron deficient dienophile, having served in 1,3-dipolar cycloadditions with nitrile oxides to give heterocycles, such as nitroisoxazoles. The cycloaddition reaction of nitroacetylene to simple monoazido compounds is fast, and can be done at room temperature. For polyazido compounds, the cycloaddition depends on the structure of the azido compound as well as the reaction conditions. The cycloaddition of nitroacetylene to azides is regioselective reaction. Several different azido compounds have been investigated and the results will be described.
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Modern Acetylene Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
