16109-68-5Relevant articles and documents
Oxidative Coupling of Aromatic Amines and Nitrosoarenes: Iodine-Mediated Formation of Unsymmetrical Aromatic Azoxy Compounds
Yu, Xiaochun,Ding, Weijie,Ge, Panyu,Wang, Shun,Wang, Jichang
supporting information, p. 3150 - 3156 (2018/08/24)
I2/DABCO (iodine/1,4-diazabicyclo[2.2.2]octane)-mediated oxidative coupling of nitrosobenzenes with aromatic amines was revealed to lead to the production of unsymmetrical aromatic azoxy compounds, instead of azo compounds reported previously in Mills reaction. Our study illustrates that various aromatic amines can be efficiently coupled with nitrosobenzenes to produce unsymmetrical azoxy product, in which more than thirty unsymmetrical azoxybenzenes have been successfully prepared. The applicability to a broad range of substrates, scalability to large scales and mild reaction conditions make this new synthetic protocol very practical, providing a convenient and direct access to unsymmetrical azoxybenzenes. (Figure presented.).
4-Hydroxy-ONN-azoxybenzene
Ejsmont, Krzysztof,Domanski, Andrzej,Kyziol, Janusz,Zaleski, Jacek
, p. 697 - 699 (2007/10/03)
The oxidation of 4-hydroxyazobenzene provided a mixture of two azoxy compounds, which were separated by column chromatography. The isomer with the higher melting point appeared to belong to the α (ONN) series, as determined by X-ray diffraction. The molecule, C12H10N2O2, is almost planar. The benzene rings are twisted by 11.7 (2) (substituted) and 4.1 (1)° (unsubstituted) with respect to the ONN plane. The molecules are connected to one another by strong O-H···O hydrogen bonds forming chains extended along [001], which are bound by much weaker C-H···O hydrogen bonds forming layers in the bc plane.
