Reduction of Nitroaromatic Compounds with Sodium Borohydride

1-Phenyl-4-imidazolidinone (Z)-Oxime

“…Nitroarenes reduced with sodium borohydride usually yield azoxy or azo compounds (Hutchins, Lamson, Rua, Milewski & Maryanoff, 1971). In other cases, treatment of aromatic nitro compounds with NaBH4 has resulted in either the reduction of the ring to cyclohexane leaving the nitro group untouched or in cleavage of the nitro group (Kaplan, 1964). In contrast, the reduction of an aliphatic nitro compound containing an o~-H atom may be stopped at the oxime stage (Patai, 1970).…”

Synthesis, and single crystal structure of fully-substituted polynitrobenzene derivatives for high-energy materials

“…In summary, a serial of novel energetic fully-substituted polynitrobenzene derivatives (6-9) were obtained by the reliable substitution of TCTNB with 1,2,4-triazole, followed by the displacement of the halogen groups with aqueous ammonia or sodium azide. Their structures were characterized by 1 H, 13 C NMR spectroscopy and HRMS. Single crystal X-ray diffraction analysis was accomplished for compounds 4-8 and delivers insights into their structural characteristics.…”

“…X-ray diffraction analysis unambiguously elucidated the structures of compounds 6, 7 and 8. Compound 9 was characterized with 1 H, 13 C NMR and HRMS.…”

“…substitution of halogens due to different nucleophilicity of azoles and steric-hindrance between substituted groups, which make the reaction unpractical and difficult to purify. [11][12][13] In general, the synthesis and characterization of fully substituted polynitrobenzenes as energetic materials are still challenging.…”

Herstellung von 1,4‐Dichlornaphtalin aus 1,4‐Dichlor‐5‐nitro‐naphtalin

“…Zwei weitere Hydrogenolysen von Nitrogruppen bei Polynitroaromaten wurden durch KAPLAN bekannt, der fand, dass bei der Einwirkung von Natriumborhydrid auf s-Trichlor-trinitro-benzol oder 1,3-Dinitro-2,4,6-trichlor-benzol je eine Nitrogruppe durch Wasserstoff ersetzt wird [4].…”