Nitric Acid → 1,1,3,5,5,7-Hexanitro-3,7-diazacyclooctane

Reaction equation

S(=O)(=O)(O)[OH:2].[N+:6]([C:9]1([N+:25]([O-:27])=[O:26])[CH2:16][NH:15][CH2:14][C:13]([N+:20]([O-:22])=[O:21])([N+:17]([O-:19])=[O:18])[CH2:12][N:11]([N:23]=[O:24])[CH2:10]1)([O-:8])=[O:7].[N+:28]([O-])([OH:30])=[O:29]>>[N+:23]([N:11]1[CH2:12][C:13]([N+:20]([O-:22])=[O:21])([N+:17]([O-:19])=[O:18])[CH2:14][N:15]([N+:28]([O-:30])=[O:29])[CH2:16][C:9]([N+:6]([O-:8])=[O:7])([N+:25]([O-:27])=[O:26])[CH2:10]1)([O-:2])=[O:24]

Participants

Reactant 3

HCID 944Nitric Acid

HCID 1118Sulfuric Acid2×

HCID 131113913,3,7,7-Tetranitro-1-nitroso-1,5-diazocane

Product 1

HCID 40641851,1,3,5,5,7-Hexanitro-3,7-diazacyclooctaneYield 90%

Procedure

To 3.4 ml concentrated sulfuric acid at 0°-5° C. in an ice bath was added 0.075 g 3,3,7,7-tetranitro-1-nitrosoperhydro-1,5-diazocine (I). To this was then added a mixture of 0.8 ml nitric acid (90 percent) and 1.4 ml concentrated sulfuric acid. The mixture was stirred in the ice bath for 15 minutes and then was poured onto ice. The solid was filtered off, washed with water, and dried in a vacuum desiccator to give 0.080 g (90 percent) of 1,3,3,5,7,7-hexanitroperhydro-1,5-diazocine. The product was recrystallized from acetonitrile or nitromethane; mp: 250° C., onset of decomposition; 1H NMR (acetone-d6): δ 5.70 (s).