A series of 1-[2-aryl-1-diazeny1]-3-({3-[2-aryl-1-diazenyl]perhydrobenzo[d]imidazol-1-yl}methyl)perhydrobenzo[d]imidazoles.: Synthesis and characterization

Reaction of diazonium salts with solutions of 1,2-diaminocyclohexane mixed with formaldehyde affords the 1-[2-aryl-1-diazenyl]-3-({3-[2-aryl-1-diazenyl]perhydrobenzo[d]imidazol-1-yl)methyl)perhydrobenzo[d]imidazoles (6), a new series of bis-triazenes with different connectivity than any previous type of bis-triazene reported. The products have been characterized principally by NMR and IR spectroscopy, elemental analysis and unequivocally by X-ray crystallography. The methylene protons of the perhydroimidazole rings are diastereotopic giving rise to a doublet of doublets pattern in the H-1 NMR spectra. However, detailed analysis of the NMR spectra shows that there is more than one set of doublet-of-doublet signals, suggesting the presence of different rotameric forms of the products. The C-13 NMR spectral assignments were assisted by COSY and DEPT experiments with selected compounds.