4504-08-9Relevant academic research and scientific papers
Synthesis of Unsymmetrical Azoxyarenes via Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines with Nitrosoarenes
Shi, Chongyang,Xu, Boxia,Fang, Xiaolan,Yu, Xiaochun,Jin, Huile,Wang, Shun
supporting information, p. 1963 - 1967 (2021/03/04)
A copper-catalyzed oxidative dehydrogenative coupling of nitrosobenzenes with anilines for the synthesis of unsymmetrical azoxybenzenes was developed. This approach uses O2 as the oxidant. The reaction products are diverse unsymmetrical azoxybe
Synthesis of Unsymmetrical Aromatic Azoxy Compounds by Silver-Mediated Oxidative Coupling of Aromatic Amines with Nitrosoarenes
Ding, Weijie,Xu, Shengshi,Yu, Xiaochun,Wang, Shun
supporting information, (2019/02/07)
A silver(I) oxide-mediated synthesis of unsymmetrical aromatic azoxy compounds has been successfully achieved, wherein oxidative coupling reactions between aromatic amines and nitrosoarenes take place in ethanol under air. This reaction has very high economic value because silver(I) oxide is the only oxidant required and no other additive is needed. The resulted silver particles can be easily recovered, while the only other byproduct is water. This new procedure is compatible with various functional groups and proceeds under mild reaction conditions.
Synthesis method of asymmetric azoxybenzene compound
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Paragraph 0067; 0068; 0069, (2018/09/08)
The invention relates to a synthesis method of an asymmetric azoxybenzene compound. According to the method, in an organic solvent, a compound system comprising iodine and an auxiliary ensures that anaromatic ammonia compound and a nitrosobenzene compound react, and a series of asymmetric azoxybenzene is specifically obtained. The method is simple in reaction, simple to operate, good in selectivity and high in yield, belongs to a new synthesis method of the asymmetric azoxybenzene compound, provides a novel synthesis route for the preparation of the compound, and has excellent scientific research value and industrial potential.
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.).
Preparation, separation and identification of some para-substituted ONN and NNO trans-azoxybenzenes
Domanski,Kyziol
, p. 1839 - 1846 (2007/10/03)
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
Photochemistry of 3- and 4-Nitrophenyl Azides: Detection and Characterization of Reactive Intermediates
Liang, Tsuei-Yun,Schuster, Gary B.
, p. 7803 - 7810 (2007/10/02)
Irradiation of nitro-substituted aromatic azides initiates a complex series of chemical reactions that lead to different products depending on the details of the experiment.There is evidence that four reactive intermediates participate in product-determining reactions.These are the singlet nitrene, the triplet nitrene, the triplet azide, and the ring-expanded dehydroazepine.The chemical and physical properties of each of these species is modified by the nitro substituent.The reactivity of the singlet nitrene with nucleophilic amines is increased, the lifetime of the dehydroazepine is shortened, and the triplet nitrene becomes a powerful single-electron acceptor.Nitro-substituted aromatic azides are widely used in photolabeling experiments.The findings of this study suggest that they may be inappropriate choices as photolabeling agents in many circumstances.
Studies on the Reactivity of Azoxybenzenes. Part 12. αβ-Interconversion of para-Monosubstituted Azoxybenzenes in the Wallach Rearrangement
Yamamoto, Jiro,Aimi, Hironori,Masuda, Yasuko,Sumida, Takashi,Umezo, Masahiro,Matuura, Teruo
, p. 1565 - 1568 (2007/10/02)
Under the reaction conditions for the Wallach rearrangement, 4-methyl-ONN-(1α), 4-methyl-NNO-(1β), 4-nitro-ONN-(2α), and 4-nitro-NNO-azoxybenzene (2β) were found to undergo αβ-interconversion, while 4-bromo-ONN-(3α) and 4-bromo-NNO-azoxybenzene (3β) do not.The αβ-interconversion occurs with both mono- and di-protonated forms of the azoxybenzenes.
AZO AND AZOXY COMPOUNDS. IV. ALKYLATION OF N-NITROSO-N-PHENYLHYDROXYLAMINE. SYNTHESIS AND MASS SPECTRA OF 1-ALKOXYDIAZENE 2-OXIDES
Yandovskii, V. N.,Misharev, A. D.,Tselinskii, I. V.,Dobrodumova, E. Yu.,Traore, U.
, p. 258 - 264 (2007/10/02)
1-Alkoxy-2-phenyldiazene 2-oxides were obtained by the reaction of the salts of N-nitroso-N-phenylhydroxylamine with primary, secondary, and tertiary alkyl bromides.The mass spectra of the compounds were studied.
