Reaction of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with electrophilic reagents: Bromine and nitric acid
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′-cyclohe...
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Published in | Russian journal of organic chemistry Vol. 49; no. 8; pp. 1208 - 1214 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Boston
Springer US
01.08.2013
Springer Nature |
Subjects | |
Online Access | Get full text |
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Summary: | 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
2,7
] tetradeca-2(7),3,5,8-tetraen-6-ol. |
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ISSN: | 1070-4280 1608-3393 |
DOI: | 10.1134/S1070428013080198 |