99686-17-6

Upstream product

• 1516-21-8 4-methoxynitrosobenzene 
• 18523-44-9 p-(dimethylamino)phenyl azide 
• 58014-26-9 [4-(4-Methoxy-phenyl-NNO-azoxy)-phenyl]-dimethyl-amine 
• 108193-69-7 C₁₅H₁₇N₃O₃ 

Downstream Products

• 99686-19-8 N-[4-(4-Methoxy-phenylazo)-phenyl]-N-methyl-formamide 

Relevant academic research and scientific papers

The Photochemistry of Some Methoxy and Dimethylamino Derivatives of Azoxybenzene

The photochemistry of the six azoxybenzene derivatives carrying a methoxy and/or a dimethylamino group in positions 4/4' has been examined in alcogols and in benzene and found to lead to different processes.The photo-Wallach rearrangement takes place for all except the disubstituted derivatives.This process involves an intermediate, which either gives back the starting azoxy or is converted to the final o-hydroxy derivative through acid catalysis as well as by the previously reported basic catalysis or via cleavage to diazonium ions, which can be trapped before recombination.Oxygen shift to yield the isomeric azoxy derivative (only one precedent known) is a general, one-way process, leading in every case to the azoxy benzene with the N->O group far from the ring carrying the stronger electron-donating substituent.Differently from the photo-Wallach rearrangement, this process shows little solvent dependence.The dimethylamino derivatives undergo also or exclusively different fragmentations, such as intramolecular hydrogen abstraction and cleavage of either the N=N or the C-N bond.The solvent and substituent effect upon electronic spectra, reaction quantum yield, and product distribution are discussed.The photochemistry is attributed to a ?,?* state with strong internal charge transfer.

Photochemical Decomposition of 4-Arylazo- and 4-Arylazoxy-N,N-dialkylaniline N-Oxides

The 4-aryl-N,N-dialkylaniline N-oxides (1a-c) decompose on u.v. irradiation in aprotic solvents, undergoing deoxygenation as well as intramolecular hydrogen abstraction, to give amides and dealkylated products.The latter process is more important for the diethyl derivative (1b) (photoCope elimination).Visible irradiation is ineffective.The 4-arylazoxy-N,N-dialkylaniline N-oxides (2a-d) undergo photochemical deoxygenation from the amino group (major process) as well as from the azo group.The mechanism of these photoprocesses is discussed in general and in relation to the possible involvement of these N-oxide derivatives in photofading of the related azo dyes.