P. S. Gribov, M. V. Mikhailova, T. S. Kon'kova, Yu. N. Matyushin, A. B. Sheremetev, “Di(propargyl)nitramine: synthesis and reactivity”, Mendeleev Commun., 2022, Volume 32, Issue 2,Pages <nobr>218

This article is cited in 7 papers

Communications

Di(propargyl)nitramine: synthesis and reactivity

P. S. Gribov^a, M. V. Mikhailova^ab, T. S. Kon'kova^c, Yu. N. Matyushin^c, A. B. Sheremetev^a

^a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b D.Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation
^c N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: 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.

Keywords: propargylation, nitramines, click reactions, alkynes, azides, 1,2,3-triazoles, nitrile oxides, isoxazoles, diazoacetates, pyrazoles.

Language: English

DOI: 10.1016/j.mencom.2022.03.021

	*Supplementary materials:*
		Supplementary_data_1.pdf	3.4 Mb