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Di(propargyl)nitramine: synthesis and reactivity

Pavel Sergeyevich Gribov 1
Pavel Sergeyevich Gribov
, 
Maria V Mikhailova 1, 2
Maria V Mikhailova
, 
Tatiana Sergeevna Kon'kova 3
Tatiana Sergeevna Kon'kova
, 
Yurii Nikolaevich Matyushin 3
Yurii Nikolaevich Matyushin
, 
Aleksei Borisovich Sheremetev 1
Aleksei Borisovich Sheremetev
10.1016/j.mencom.2022.03.021
Published 2022-03-06
Communication , Volume 32, Issue 2, 218-220
8
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Gribov P. S. et al. Di(propargyl)nitramine: synthesis and reactivity // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 218-220.
GOST all authors (up to 50) Copy
Gribov P. S., Mikhailova M. V., Kon'kova T. S., Matyushin Y. N., Sheremetev A. B. Di(propargyl)nitramine: synthesis and reactivity // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 218-220.
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TY - JOUR
DO - 10.1016/j.mencom.2022.03.021
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.021
TI - Di(propargyl)nitramine: synthesis and reactivity
T2 - Mendeleev Communications
AU - Gribov, Pavel Sergeyevich
AU - Mikhailova, Maria V
AU - Kon'kova, Tatiana Sergeevna
AU - Matyushin, Yurii Nikolaevich
AU - Sheremetev, Aleksei Borisovich
PY - 2022
DA - 2022/03/06
PB - Mendeleev Communications
SP - 218-220
IS - 2
VL - 32
ER -
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@article{2022_Gribov,
author = {Pavel Sergeyevich Gribov and Maria V Mikhailova and Tatiana Sergeevna Kon'kova and Yurii Nikolaevich Matyushin and Aleksei Borisovich Sheremetev},
title = {Di(propargyl)nitramine: synthesis and reactivity},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.021},
number = {2},
pages = {218--220},
doi = {10.1016/j.mencom.2022.03.021}
}
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Gribov, Pavel Sergeyevich, et al. “Di(propargyl)nitramine: synthesis and reactivity.” Mendeleev Communications, vol. 32, no. 2, Mar. 2022, pp. 218-220. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.021.

Keywords

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

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.

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