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

✍ Scribed by Julie F. Glister; Keith Vaughan

Publisher: Journal of Heterocyclic Chemistry
Year: 2006
Tongue: English
Weight: 112 KB
Volume: 43
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570430134

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✦ Synopsis

Abstract

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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 ^1^H 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 ^13^C NMR spectral assignments were assisted by COSY and DEPT experiments with selected compounds.

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