17310-79-1

Upstream product

• 949-87-1 4-Methylazobenzol 
• 98-95-3 nitrobenzene 
• 17310-78-0 β-p-methylazoxybenzene 
• 16046-28-9 N-Phenyl-N'-tosyloxydiimid-N-oxid 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 16046-28-9 N'-p-Toluolsulfonyloxy-N-phenyl-diimid-N-oxid 
• 106-49-0 p-toluidine 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 111078-57-0 4-phenyl-ONN-azoxybenzoic acid 
• 20773-92-6 2-p-Tolylazo-phenol 
• 582-85-4 5-Methyl-2-phenylazo-phenol 
• 949-87-1 4-Methylazobenzol 
• 96217-83-3 N'-(4-bromo-phenyl)-N-p-tolyl-diazene-N-oxide 
• 2497-33-8 4-((4-methylphenyl)azo)phenol 

Relevant academic research and scientific papers

Synthesis of Unsymmetrical Azoxyarenes via Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines with Nitrosoarenes

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

Rh(III)-Catalyzed Regio- and Chemoselective [4 + 1]-Annulation of Azoxy Compounds with Diazoesters for the Synthesis of 2H-Indazoles: Roles of the Azoxy Oxygen Atom

A Rh(III)-catalyzed tandem C-H alkylation/intramolecular decarboxylative cyclization of azoxy compounds with diazoesters for the synthesis of 3-acyl-2H-indazoles is disclosed. The azoxy instead of the azo group enables a distinct approach for cyclative capture, leading to a [4 + 1]-annulation rather than a classic [4 + 2] manner. The azoxy oxygen atom is traceless after annulation, and further removal from the product is not required. This reaction features a complete regioselectivity for unsymmetrical azoxybenzenes and a compatibility of monoaryldiazene oxides.

Rh(III)-Catalyzed [4 + 1]-Annulation of Azoxy Compounds with Alkynes: A Regioselective Approach to 2H-Indazoles

A rhodium-catalyzed regioselective C-H activation/cyclization of azoxy compounds with alkynes has been disclosed to construct a variety of 2H-indazoles. A [4 + 1]-cycloaddition rather than a normal [4 + 2] mode is observed in the process of cyclative capture along with an oxygen-atom transfer and a C≡C triple bond cleavage. This protocol features a broad substrate scope, a good functional group tolerance, and an exclusive regioselectivity.

Perfluoroalkylation of azo compounds

Perfluoroalkyl azo dyes were prepared by the reaction of azo compounds with bis(perfluoroalkanoyl) peroxides.The absorption spectra and melting points of the perfluoroalkyl azo dyes were also examined.

Aryliminodimagnesium Reagents. IV. The Independent Preparation of Unsymmetrically Substituted Azoxyarene Isomers and Their Deoxygenation

By use of the condensation reaction of aryliminodimagnesium reagents (ArN(MgBr)2) with nitroarenes, six symmetrical and eight unsymmetrical azoxyarenes including four pairs of isomers were prepared in 40-80percent yields.The deoxygenation reaction of the azoxyarenes by treating with five molar equivalents of p-MeOC6H4N(MgBr)2 at 55 deg C in tetrahydrofuran was also studied, and the reactivity of deoxygenation was correlated to the shift of the electronic absorption maximum of azoxyarene.

Studies on the Reactivity of Azoxybenzenes. Part 12. αβ-Interconversion of para-Monosubstituted Azoxybenzenes in the Wallach Rearrangement

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.

SYNTHESIS OF AZOXYBENZENE-SbCl5 COMPLEXES AND THEIR SELECTIVE ORTHO-WALLACH REARRANGEMENT

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.