Efficient synthesis of N-(chloromethyl)nitramines via TiCl4-catalyzed chlorodeacetoxylation

Gribov, Pavel S.; Suponitsky, Kyrill Yu.; Sheremetev, Aleksei B.

doi:10.1039/d2nj03521a

Cited by 9 publications

(5 citation statements)

References 44 publications

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“…Most of the reagents and starting materials were purchased from commercial sources and used without additional purification. The starting compound 6 [46] and 8a,b [50] were synthesized by using previously reported procedures.…”

Section: Methodsmentioning

confidence: 99%

“…We, therefore, have investigated the chlorine displacement in N,N -bis(chloromethyl)nitramine 8 with propargyl alcohol. To establish optimal conditions, we used readily available 1,6-dichloro-2,5dinitro-2,5-diazahexane (8a) [50] and propargyl alcohol as our exemplar reagent set (Scheme 3). Scheme 3.…”

Section: Synthesis and Characterization Of Monomers And Polymermentioning

confidence: 99%

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Energetic Polymer Possessing Furazan, 1,2,3-Triazole, and Nitramine Subunits

Gribov

Kondakova

Il’icheva

et al. 2023

IJMS

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A [3 + 2] cycloaddition reaction using dialkyne and diazide comonomers, both bearing explosophoric groups, to synthesize energetic polymers containing furazan and 1,2,3-triazole ring as well as nitramine group in the polymer chain have been described. The developed solvent- and catalyst-free approach is methodologically simple and effective, the comonomers used are easily available, and the resulting polymer does not need any purification. All this makes it a promising tool for the synthesis of energetic polymers. The protocol was utilized to generate multigram quantities of the target polymer, which has been comprehensively investigated. The resulting polymer was fully characterized by spectral and physico-chemical methods. Compatibility with energetic plasticizers, thermochemical characteristics, and combustion features indicate the prospects of this polymer as a binder base for energetic materials. The polymer of this study surpasses the benchmark energetic polymer, nitrocellulose (NC), in a number of properties.

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Section: Methodsmentioning

confidence: 99%

Section: Synthesis and Characterization Of Monomers And Polymermentioning

confidence: 99%

Energetic Polymer Possessing Furazan, 1,2,3-Triazole, and Nitramine Subunits

Gribov

Kondakova

Il’icheva

et al. 2023

IJMS

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“…Most of the reagents and starting materials were purchased from commercial sources and used without additional purification. The starting chloromethylnitramines [22] were synthesized by using previously reported procedures.…”

Section: Methodsmentioning

confidence: 99%

“…In the course of our work on functionalized nitramines [15,[17][18][19][20][21][22], we focused on available chloromethylnitramines 1 and envisioned nucleophilic substitution of chlorine by haloalcohols, which would give nitramino ethers 2 the halogen atom in which can be replaced by an azide group (Scheme 1). This expectation was based on the possibility, reported by Frankel et al [13], of replacing the chlorine atom in chloromethylnitramines with sterically unencumbered chloroethanol, which occurred during prolonged refluxing (up to 120 h) in dichloroethane (DCE) and gave a crude mixture contained ca.…”

Section: Synthesismentioning

confidence: 99%

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Promising Oxygen- and Nitrogen-Rich Azidonitramino Ether Plasticizers for Energetic Materials

et al. 2022

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A simple, mild and general method has been developed for the preparation of alkyl nitramines bearing a halogenoalkoxylic moiety. From these reactive halogen intermediates, a few azidoalkoxyl alkyl nitramines have been produced as energetic plasticizers. This simple protocol allows azidonitramino ether plasticizers to be obtained from available precursors in high yields, as it is safe and viable for large-scale operations. The resulting products have been fully characterized by spectral methods, and their impact sensitivity, thermal transformations and burning properties were determined, thus allowing complete comparison to the analogues including other combinations of structural units. Such characterization of these new plasticizers illustrates the extent to which the nature and position of the functional units can be used to tune the above properties of these nitramines. All azidonitramino ethers are liquid with excellent energetic performance and are promising candidates for new environmentally friendly energetic materials.

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