Synthesis of heterobicyclic tetrakis- and bis-triazenes: Reaction between 3,3′-ethane-1,2-diylbis(1,3,5-triazabicyclo[3.2.1]octane) (ETABOC) with diazonium salts bearing electron donating groups

Abstract In this work, a coupling reaction of aryl diazonium salts with a poly-N-nucleophile is developed for the synthesis of a variety of heterobicyclic tetrakis- and bistriazene compounds. The transformation proceeds smoothly in basic medium with good and moderate yields. In addition to the expected 3,3′-methanediylbis{1,5-bis[(E)-aryldiazenyl]-1,3,5-triazepanes}, two classes of heterobicyclic bis-triazenes were obtained by two ring rearrangement reactions. Using this method, an unknown class of organic compounds containing the saturated bis(imidazolidinyl)-methane unit can be accessed efficiently.