314751-18-3

Upstream product

• 31789-78-3 N²-p-Toluolsulfonyl-N¹-(4'-hydroxyphenyl)benzamidin 
• 494210-56-9 4-Methyl-N-[1-(4-oxo-cyclohexa-2,5-dienylideneamino)-1-phenyl-meth-(Z)-ylidene]-benzenesulfonamide 
• 307553-77-1 N-[1-(3-Chloro-4-hydroxy-phenylamino)-1-phenyl-meth-(Z)-ylidene]-4-methyl-benzenesulfonamide 

Downstream Products

• 307553-74-8 N-[1-(3,5-Dichloro-4-oxo-cyclohexa-2,5-dienylideneamino)-1-phenyl-meth-(Z)-ylidene]-4-methyl-benzenesulfonamide 
• 307553-78-2 4-Methyl-N-[1-phenyl-1-(2,3,5-trichloro-4-hydroxy-phenylamino)-meth-(Z)-ylidene]-benzenesulfonamide 
• 308292-17-3 4-Methyl-N-[1-phenyl-1-(2,3,5,6-tetrachloro-4-oxo-cyclohexa-2,5-dienylideneamino)-meth-(Z)-ylidene]-benzenesulfonamide 
• 307553-79-3 4-Methyl-N-[1-phenyl-1-(2,3,5,6-tetrachloro-4-hydroxy-phenylamino)-meth-(Z)-ylidene]-benzenesulfonamide 

Relevant academic research and scientific papers

Chlorination of N-(N-arylsulfonylarylimidoyl)-1,4-benzoquinone imines and their reduced forms

The study of chlorination of N-(N-arylsulfonylarylimidoyl)-1, 4-benzoquinone imines and of N-(N-arylsulfonylarylimidoyl)-1,4-aminophenols revealed that the dominant stage in the process was the formation of cyclohexene structures, 4-(N-arylsulfonylarylimidoyl)imino-2,5,6-trichloro-2-cyclohexene-1-ones, resulting from addition of a Cl2 molecule across the C=C bond of the quinoid ring. These substances suffer a prototropic rearrangements yielding N-(N-arylsulfonylarylimidoyl)-2,3,6-trichloro-4-aminophenols. The latter are the most common reaction products. The products of deeper chlorination were also obtained.

Hydrochlorination and hydrobromination of N-(N-arylsulfonylbenzimidoyl)-1,4-benzoquinonimines

The direction of hydrohalogenation of N-substituted p-quinonimines was predicted on the basis of orbital coefficients of the C2 and C3 atoms in the lowest unoccupied molecular orbital, calculated by the PM3 method. It was assumed that the reaction is orbital-controlled and that the initial act of hydrohalogenation is nucleophilic attack by halide ion. The proposed approach was verified by experimental hydrochlorination and hydrobromination of N-(N-arylsulfonylbenzimidoyl)-1,4-benzoquinonimines which take up HHlg molecule following the 1,4-addition scheme, i.e., the halogen atom adds to C2 of the quinoid ring.