Reduction of 1,2‐Bis[(Z)‐(2‐nitrophenyl)‐NNO‐azoxy]benzene1: Synthesis of Cyclotrisazobenzene ( = (5E,6aZ,11E,12aZ,17E,18aZ)‐5,6,11,12,17,18‐Hexaazatribenzo[aei][1,3,5,7,9,11]cyclododeca‐hexaene)Na2S reduction of 1,2‐bis[(Z)‐(2‐nitrophenyl)‐NNO‐azoxy]benzene (2) yielded 3 deoxygenated products: the (known) red 2,2′‐((E,E)‐1,2‐phenylenbisazo)dianiline (3, 23%), the orange 2‐[2‐((E)‐2‐aminophenylazo)phenyl]‐2H‐benzotriazol (4, 55%) and the colorless 2,2′‐(1,2‐phenylene)di‐2H‐benzotriazol (5, 13%). The constitutions of 3–5 and of 6, the N‐acetyl derivative of 4, were deduced from their 1H‐NMR spectra (chemical shifts, couplings, and symmetry properties), and the configurations of 3, 4, and 6 at their N,N‐double bonds are assumed to be the same as in 2. Oxidation of 3 with 2 mol‐equiv. of Pb(OAc)4 afforded 5 (47%) and a novel, highly symmetrical macrocycle, called cyclotrisazobenzene (7, 24%). The constitution of 7 as a tribenzo‐hexaaza[12]annulene and its (E)‐configuration at the N,N‐bonds was confirmed by X‐ray analysis. The molecular symmetry expressed by the 1H‐, 13C‐ and 15N‐NMR spectra of 7 reveals a rapid torsional motion around the six N,C bonds. This implies that the N,N‐double bonds in the cyclic 12π‐electron system (or 24π‐electron system if the benzene rings are included) of 7 are highly localized.