Di(propargyl)nitramine: synthesis and reactivity

An improved synthesis of (propargyl)nitramine and its pioneering conversion to di(propargyl)nitramine involve the alkylation of NH nitramines with propargyl halides or tosylate as the key steps. The standard (p° = 0.1 MPa) molar enthalpy of formation at 298.15 K for di(propargyl)nitramine was determined from the experimental standard molar energy of combustion in oxygen, measured by static bomb combustion calorimetry. Propargyl nitramines are suitable substrates for 1,3-dipolar cycloaddition reactions with azides, nitrile oxides and diazo compounds.