Journal
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
Volume 49, Issue 9, Pages 1358-1369Publisher
SPRINGER
DOI: 10.1007/s10593-013-1385-z
Keywords
adamantanes; furazans; electrophilic reactions; X-ray structural analysis
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Funding
- Department of Chemistry and Materials Science, Russian Academy of Sciences [OKhNM-04]
- Russian Foundation for Basic Research [12-03-12012 OFI-M]
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The reactivity of 3-(1-adamantyl)-4-aminofurazan was studied. Upon treatment with oxidizing reagents the amino group is oxidized to azo, azoxy, and nitro groups. The nitration of 3-(1-adamantyl)-4-aminofurazan with nitric acid provided the corresponding nitroamine. The reaction of 3-(1-adamantyl)-4-nitrofurazan with nitrating and bromination agents takes place at the bridgehead position of the adamantane fragment and gives the corresponding nitroxyl and bromo derivatives. An X-ray structural analysis of 4,4'-di(1-adamantyl)azofurazan was undertaken.
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