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Energetic polymers salts from 1‐vinyl‐1,2,4‐triazole derivatives have been synthesized via free radical polymerization of 1‐vinyl‐1,2,4‐triazolium monomer salts or by protonation of poly(1‐vinyl‐1,2,4‐triazole) with inorganic or organic acids. Standard enthalpies of formation of the new monomer salts were calculated using the computationally feasible DFT(B3LYP) and MP2 methods in conjunction with an empirical approach based on densities of salts. Compared with the monomer salts, the polymer salts have good thermal properties with high densities > 1.5 g cm−3. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 2414–2421, 2008

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“…( 1 ) 1‐Vinyl‐1,2,4‐triazole : Compound 1 was prepared by a literature procedure 11. A colorless oil is obtained, 90% yield, bp 103 °C (15 Torr).…”

Section: Methodsmentioning

confidence: 99%

Energetic polymer salts from 1‐vinyl‐1,2,4‐triazole derivatives

Xue

Gao

Shreeve

2008

J. Polym. Sci. A Polym. Chem.

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“…Hg6 and Pd-mediated7 preparations of vinyl azoles and vinyl ethers are notable in this case. The toxicity of mercury and the high cost of Pd, as well as the latter’s air sensitivity, potentially limit their use for many industrial applications.…”

mentioning

confidence: 85%

First Application of an Efficient and Versatile Ligand for Copper-Catalyzed Cross-Coupling Reactions of Vinyl Halides with N-Heterocycles and Phenols

et al. 2009

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2-Pyridin-2-yl-1H-benzoimidazole L3 is presented as a new, efficient, and versatile bidentate N-donor ligand suitable for the copper-catalyzed formation of vinyl C-N and C-O bonds. This inexpensive and easily prepared ligand facilitates copper-catalyzed cross-coupling reactions of alkenyl bromides and iodides with N-heterocycles and phenols to afford the desired cross-coupled products in good to excellent yields with full retention of stereochemistry. This method is particularly noteworthy given its efficiency i.e., mild reaction conditions, low catalyst loading, simplicity, versatility, and exceptional level of functional group tolerance.

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“…presence of the mercuric acetate-trifluoroacetic acid catalytic system at 70°C the reaction takes place with the complete absence of side processes and gives 4-nitro-1-vinyl-5-R-1,2,3-triazoles 60 with yields of 70-88%[67].…”

mentioning

confidence: 99%

Synthesis and properties of nitro-1,2,3-triazoles (Review)

Vereschagin

Pokatilov

Kizhnyaev

2008

Chem Heterocycl Comp

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Published data on methods for the synthesis of substituted 4(5)-nitro-1,2,3-triazoles and their properties are reviewed.Against the background of the extremely large amount of published information about methods for the production of vicinal triazoles and their properties the chemistry of nitro-substituted triazoles of this series is in an embryonic state. At the same time, according to existing data, vicinal nitrotriazoles may find use in the synthesis of medicines, dyes, agents for the struggle against agricultural pests, energy-rich components of propellants, special-purpose powders, and in other regions of technology. However, the practical application of these compounds has been restrained by the lack of technologically convenient methods for their production. Until now sufficiently effective preparative methods have not been developed for their synthesis. With respect to their properties it is known only that the nitro group of the triazoles is capable of being reduced catalytically to an amino group and substituted by various nucleophilic fragments, while the triazole ring is alkylated by alkyl halides and adds to an activated multiple bond. The limited information is probably explained by the poor availability of vicinal nitrotriazoles, which is most likely due to the passivity of the 1,2,3-triazole in electrophilic substitution reactions at carbon atoms and particularly in nitration processes. In this connection it seems expedient to examine methods for the synthesis of nitro-substituted 1,2,3-triazoles by direct nitration with due regard to the conditions determining the entry of the nitro group into the azole ring and also methods for the construction of nitrotriazoles by the cyclization of open-chain nitro compounds and to assess their properties. SYNTHESIS OF NITRO-1,2,3-TRIAZOLES Nitration of 1,2,3-TriazolesThe inertness of the carbon atoms of the triazole ring toward electrophilic reagents is due to distribution of the electron density of the ring in such a way that the carbon atoms carry a partial positive charge, preventing the addition of a nitronium cation. Therefore, the path to direct nitration of the ring of unsubstituted vicinal triazole has not so far been realized. Attempts to introduce a nitro group into the ring of the heterocycle of 1-phenyl-and 4-phenyl-1,2,3-triazoles were unsuccessful. 1-Phenyl-1,2,3-triazole (1) does not form 4(5)-nitrosubstituted triazole during nitration even under rigid conditions. Here, only the phenyl ring is nitrated-initially at the para position and then at the ortho position [1-3].

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Cited by 37 publications

References 1 publication

Energetic polymer salts from 1‐vinyl‐1,2,4‐triazole derivatives

Energetic polymer salts from 1‐vinyl‐1,2,4‐triazole derivatives

First Application of an Efficient and Versatile Ligand for Copper-Catalyzed Cross-Coupling Reactions of Vinyl Halides with N-Heterocycles and Phenols

Synthesis and properties of nitro-1,2,3-triazoles (Review)

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