105949-69-7Relevant academic research and scientific papers
Open chain nitrogen compounds. Part XI. 3,7-Bis(arylazo)-1,3,5,7-tetraazabicyclononanes: the reaction of diazonium ions with ammonia-formaldehyde mixtures
Singer, Robert D.,Vaughan, Keith,Hooper, Donald L.
, p. 1567 - 1572 (2007/10/02)
Reaction of a series of diazonium salts with either hexamine or an aqueous mixture of ammonia-formaldehyde affords 3,7-bis(arylazo)-1,3,5,7-tetraazabicyclononanes; several new examples of this novel class of bicycloheterocycle have been prepared and characterized.Analysis of the low-temperature nmr spectra of one compound in this series shows that the bicyclic system prefers the chair-chair conformation.The bis(arylazo)tetraazabicyclononanes, which are surprisingly stable in aqueous buffer compared to analogous triazenes of open-chain structure, do undergo slow decomposition at slight acidic pH in an acetone-buffer mixture.The apparent product of this decomposition is the arylamine, which is observed as the Mannich condensation product, ArNH.CH2CH2COCH3.
