3-(Nitramino)acrylates: synthesis and reactivity

Lipilin, Dmitry L.; Шереметев, А. Б.

doi:10.1007/s11172-022-3621-0

Cited by 4 publications

(1 citation statement)

References 33 publications

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“…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%

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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