[1,2,5]Oxadiazolo[3,4-d]pyridazine 1,5,6-trioxides: efficient synthesis via the reaction of 3,4-bis(hydroxyimino)methyl)-1,2,5-oxadiazole 2-oxides with a mixture of concentrated nitric and trifluoroacetic acids and structural characterization

An efficient synthesis of [1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxides (1) from 3,4-bis(hydroxyimino)methyl)-1,2,5-oxadiazole 2-oxides using a mixture of concentrated nitric and trifluoroacetic acids has been developed. The scope of the unconventional reaction was established. The 4,7-dinitro[1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxide 1f represents a new high energy compound, unfortunately with low thermal stability. The parent [1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxide 1c was studied by single-crystal X-ray diffraction analysis which revealed a planar molecule with an unusually long intracyclic N–N bond of 1.668(5) Å and unexpected exo-cyclic bond angles at the nitroxyl nitrogen atoms. In the crystal, the molecules of 1c are bound to each other by strong π-π stacking and C–H⋯O hydrogen bonding interactions into a three-dimensional framework that results in a high crystal density of 1.833 gcm−3. © 201

Synthesis and structural investigation of 4,4′-dimethyl-[3,3′-bi(1,2,5-oxadiazole)] 5,5′-dioxide

The oxidation of hexane-2,3,4,5-tetraone tetraoxime with dinitrogen tetroxide was studied in different solvents. The primary furoxan ring closure was found to occur involving either two central or two terminal oxime groups to form 4,7-dimethyl[1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxide and the previously unknown 4,4′-dimethyl-[3,3′-bi(1,2,5-oxadiazole)] 5,5′-dioxide. The structure of the latter compound was established by X-ray diffraction. © 2018, Springer Science+Business Media, LLC, part of Springer Nature

[1,2,5]Oxadiazolo[3,4-d]pyridazine 1,5,6-trioxides: efficient synthesis via the reaction of 3,4-bis(hydroxyimino)methyl)-1,2,5-oxadiazole 2-oxides with a mixture of concentrated nitric and trifluoroacetic acids and structural characterization

An efficient synthesis of [1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxides (1) from 3,4-bis(hydroxyimino)methyl)-1,2,5-oxadiazole 2-oxides using a mixture of concentrated nitric and trifluoroacetic acids has been developed. The scope of the unconventional reaction was established. The 4,7-dinitro[1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxide 1f represents a new high energy compound, unfortunately with low thermal stability. The parent [1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxide 1c was studied by single-crystal X-ray diffraction analysis which revealed a planar molecule with an unusually long intracyclic N–N bond of 1.668(5) Å and unexpected exo-cyclic bond angles at the nitroxyl nitrogen atoms. In the crystal, the molecules of 1c are bound to each other by strong π-π stacking and C–H⋯O hydrogen bonding interactions into a three-dimensional framework that results in a high crystal density of 1.833 gcm−3. © 201