J. Glister, K. Vaughan
2006
Citations
0
Influential Citations
12
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
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 1H 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 13C NMR spectral assignments were assisted by COSY and DEPT experiments with selected compounds.