- 3,3-Dinitratooxetane - an important leap towards energetic oxygen-rich monomers and polymers
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3-Substituted oxetanes are valuable monomers for modern ring-opening polymerizations. A new solid-state oxidizer, 3,3-dinitratooxetane (C3H4N2O7), which has an oxygen content of 62.2% was synthesized by the addition of N2O5to oxetan-3-one. Monoclinic single crystals suitable for X-ray diffraction (ρ1.80 g cm?3) were obtained by recrystallization from dichloromethane. In addition, 3-nitratooxetane was prepared by an improved method and 3-nitrato-3-methyloxetane was synthesized for the first time. Theoretical calculations were computed by the EXPLO5 software and additionally sensitivities towards impact and friction were determined.
- Born, Max,Fessard, Thomas C.,G?ttemann, Lucas,Klap?tke, Thomas M.,Stierstorfer, J?rg,Voggenreiter, Michael
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- Synthesis of heterocyclic geminal nitro azides
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The oxidative azidation reactions of C-nitro-substituted saturated heterocyclic compounds, viz., the nitro derivatives of oxetane, azetidine, 1,3-dioxane, tetrahydro-1,3-oxazine, and hexahydropyrimidine, were investigated. A novel representatives of the geminal nitro azides were prepared and their physicochemical properties were studied. The process of the formation of the geminal dinitro compounds upon oxidative azidation was analyzed.
- Katorov,Rudakov,Zhilin
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p. 2311 - 2317
(2014/05/06)
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- Synthesis of geminal dinitro compounds
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Geminal dinitro compounds are prepared by reacting an organic nitro compound having a replaceable hydrogen on the carbon to which the nitro group is attached with a source of nitrite ions in the presence of an oxidizing agent and a catalytic amount of an alkali metal ferricyanide.
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- Catalyzed Oxidative Nitration of Nitronate Salts
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Nitronate salts are converted to gem-dinitro compounds with nitrite ion and persulfate, in the presence of a catalytic amount of ferricyanide.The use of cyanide or sulfinate salts in place of nitrile gave gem-cyanonitro compounds and α-nitro sulfones, respectively.
- Garver, Lee C.,Grakauskas, V.,Baum, Kurt
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p. 1699 - 1702
(2007/10/02)
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- Synthesis of Electron-Deficient Oxetanes. 3-Azidooxetane, 3-Nitrooxetane, and 3,3-Dinitrooxetane
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A facile synthesis of 3-hydroxyoxetane is described and is based on the addition of acetic acid to epichlorohydrin, protection of the resulting primary alcohol as an acetal, basic acetate hydrolysis and ring closure, and removal of the protecting group. 3-Azidooxetane was prepared from 3-(tosyloxy)oxetane and sodium azide.Reduction of the azide with triphenylphosphine or hydrogen gave 3-aminooxetane, and oxidation of the amine with m-chloroperbenzoic acid gave 3-nitrooxetane.Oxidative nitration or reaction with tetranitromethane gave 3,3-dinitrooxetane. 3-Azidooxetane and 3,3-dinitrooxetane were polymerized with Lewis acids.
- Baum, Kurt,Berkowitz, Phillip T.,Grakauskas, Vytautas,Archibald, Thomas G.
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p. 2953 - 2956
(2007/10/02)
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