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- Title
Reaction of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with electrophilic reagents: Bromine and nitric acid.
- Authors
Samsonov, V.; Gatilov, Yu.; Savel'ev, V.
- Abstract
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[3 H-[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] tetradeca-2(7),3,5,8-tetraen-6-ol.
- Subjects
BENZIMIDAZOLES; CYCLOHEXANE; ELECTROPHILES; BROMINE; NITRIC acid; HYDROGEN atom; BROMINATION; ISOMERIZATION
- Publication
Russian Journal of Organic Chemistry, 2013, Vol 49, Issue 8, p1208
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428013080198