Reactions of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with bromine and nitric acid lead to the electrophilic substitution of the hydrogen atom in the meta-position with respect to the nitro group. At thebromination the primarily formed 4-bromo-6-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide when kept in the solution loses an oxygen atom forming 4-bromo-6-nitrospiro[benzimidazole-2,1′-cyclohexane] 1-oxide and an isomerization product, 8-bromo-6-nitrospiro[3H-[2,1,4]benzoxadiazine-3,1′-cyclohexane] 4-oxide. The latter exposed to light turns into 4-bromo-6-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide. The reaction of the initial 1,3-dioxide with nitric acid afforded 4,6-dinitrospiro[benzimidazole-2,1′-cyclohexan]-7-ol 1-oxide whose heating in o-dichlorobenzene resulted in 3,5-dinitro-1,8-diazatricyclo[7.5.0.0^2,7] tetradeca-2(7),3,5,8-tetraen-6-ol.

中文翻译：

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5-硝基螺[苯并咪唑-2,1'-环己烷] 1,3-二氧化物与亲电子试剂：溴和硝酸的反应

5-硝基螺并[苯并咪唑-2，1'-环己烷] 1，3-二氧化物与溴和硝酸的反应导致相对于硝基在间位的氢原子发生亲电取代。在溴化反应中，最初形成的4-溴-6-硝基螺[苯并咪唑-2,1'-环己烷] 1,3-二氧化物当保留在溶液中时会失去一个氧原子，从而形成4-溴-6-硝基螺[苯并咪唑-2,1 ′-环己烷] 1-氧化物和异构化产物8-溴-6-硝基螺[3 H- [2,1,4]苯并恶二嗪-3,1'-环己烷] 4-氧化物。后者暴露于光下变成4-溴6-硝基螺[苯并咪唑-2，1'-环己烷] 1，3-二氧化物。初始的1，3-二氧化物与硝酸反应，得到4，6-二硝基螺并[苯并咪唑-2，1′-环己基] -7-醇1-氧化物，在室温下加热。邻二氯苯生成3,5-二硝基-1,8-二氮杂三环[7.5.0.0 ^2,7 ]十四碳-2（7），3,5,8-四烯-6-醇。