N-Propargyl nitramines: synthesis and structure

In the presence of alkali in DMF, propargyl bromide and propargyl tosylate participate in the N- and O-alkylation of the nitramino group, giving N—R—N-propargylnitramines and 1-propargyloxy-2-R-diazene 1-oxides. Most of O-propargyl derivatives are unstable and decompose in the reaction medium; however, an O-propargylation product was isolated. All products were characterized by multinuclear NMR spectroscopy. Two compounds were studied by X-ray diffraction analysis.