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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Bibliographic Details
Published in:Russian journal of organic chemistry Vol. 49; no. 8; pp. 1208 - 1214
Main Authors: Samsonov, V. A., Gatilov, Yu. V., Savel’ev, V. A.
Format: Journal Article
Language:English
Published: Boston Springer US 01.08.2013
Springer Nature
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Organic Chemistry
Physical Sciences
Science & Technology
Bromine
Furoxane
Benzimidazole
Cyclohexane
Electrophilic Substitution
ISSN:1070-4280, 1608-3393
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.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428013080198