- Oxidative Coupling of Aromatic Amines and Nitrosoarenes: Iodine-Mediated Formation of Unsymmetrical Aromatic Azoxy Compounds
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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.).
- Yu, Xiaochun,Ding, Weijie,Ge, Panyu,Wang, Shun,Wang, Jichang
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supporting information
p. 3150 - 3156
(2018/08/24)
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- Preparation, separation and identification of some para-substituted ONN and NNO trans-azoxybenzenes
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A series of para-substituted azoxybenzenes was obtained as model compounds for the investigation on the mechanism of Wallach rearrangement. Oxidation of azobenzenes with hydrogen peroxide in acetic acid solution, provided mixtures of α and β isomers. Some
- Domanski,Kyziol
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p. 1839 - 1846
(2007/10/03)
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- 4-Hydroxy-ONN-azoxybenzene
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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.
- Ejsmont, Krzysztof,Domanski, Andrzej,Kyziol, Janusz,Zaleski, Jacek
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p. 697 - 699
(2007/10/03)
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- SYNTHESIS OF AZOXYBENZENE-SbCl5 COMPLEXES AND THEIR SELECTIVE ORTHO-WALLACH REARRANGEMENT
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When an equimolar solution of various azoxybenzenes and SbCl5 in carbon tetrachloride were mixed, a 1:1 complex immediately deposited as orange crystals in high yield.The thermal reaction of these complexes in inert solvents gives o-hydroxy-azobenzene selectively.On the contrary, other Lewis acids, such as TiCl4, AlCl3, FeCl3 and ZnBr2 failed to give an isolatable complex with azoxybenzene, and their direct thermal reaction with azoxybenzene resulted in deoxygenation to yield azobenzene as a main product.
- Yamamoto, Jiro,Nishigaki, Yukihiro,Umezu, Masahiro,Matsuura, Teruo
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p. 3177 - 3180
(2007/10/02)
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