Synthesis and characterization of novel triazenes from the reaction of the cyclic aminal 1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecane (TATU) with diazonium ions

The reaction of the cyclic aminal 1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecane (TATU, 4) with diazonium salts resulted in the formation of a new series of bis-triazenes, namely 3,8-bis[(4-methoxyphenyl)diazenyl]-1,3,6,8-tetraazabicyclo[4.3.1]decane 6a, 3,8-bis[(2-methoxyphenyl)diazenyl]-1,3,6,8-tetraazabicyclo[4.3.1]decane 6b, 3,8-bis(p-tolyldiazenyl)-1,3,6,8-tetraazabicyclo[4.3.1]decane 6c. When aniline derived diazonium salt 5d was coupled with TATU, 3,8-bis(phenyldiazenyl)-1,3,6,8-tetraazabicyclo[4.3.1]decane 6d and bis[1,5-bis-((E)-phenyldiazenyl)-1,3,5-triazepan-3-yl]methane 7 were obtained. These compounds were characterized by HR-MS, 1H and 13C NMR and 2D-NMR. Additionally, the structure of compound 7 was confirmed by X-ray crystallography.