76165-53-2

Upstream product

• 41595-29-3 N,N'-ditosyl-p-phenylenediamine 
• 2654-68-4 4-chloro-N-(4-(((4-chlorophenyl)sulfonyl)amino)phenyl)benzenesulfonamide 
• 98472-75-4 N,N'-bis-p-chlorobenzenesulfonyl-2-chloro-1,4-phenylenediamine 
• 2654-77-5 N,N′-(cyclohexa-2,5-diene-1,4-diylidene)bis-(4-chlorobenzenesulfonamide) 
• 173097-12-6 2,3,5,5,6,6-Hexachloro-1,4-di-p-tolylsulfonylimino-2-cyclohexene 
• 67-56-1 methanol 
• 76165-36-1 N,N'-bis-p-toluenesulfonyl-2,3,5,6-tetrachloro-1,4-benzoquinone diimine 
• 624-18-0 benzene-1,4-diamine hydrochloride 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 106-50-3 1,4-phenylenediamine 

Downstream Products

• 173097-12-6 2,3,5,5,6,6-Hexachloro-1,4-di-p-tolylsulfonylimino-2-cyclohexene 
• 76165-36-1 N,N'-bis-p-toluenesulfonyl-2,3,5,6-tetrachloro-1,4-benzoquinone diimine 

Relevant academic research and scientific papers

Reaction of N-Arylsulfonyl-p-quinonimines and semiquinoid structures produced therefrom with Bis(p-dimethylaminophenyl)phosphinite

N-Arylsulfonyl-1,4-benzoquinonemonoimines react with bis(N-dimethylaminophenyl)phosphinite in keeping with the character and position of substituents in the quinoid ring along 1,4-, 6,1-, or 1,2-addition way; N-arylsulfonyl-1,4-naphthoquinonemonoimines react along 1,4-, 6,1-, 1,2-, or 6,3-addition. Semiquinoid polyhalostructures generated therefrom react similarly to the corresponding quinonimines possessing several chlorine substituents in the quinoid ring. N,N-Diarylsulfonyl-1,4-benzoquinonediimines with no substituents in the ring yield with bis(p-dimethylaminophenyl)phosphinite 1,4-addition products. Along a competing reaction quinonediimine is reduced to the corresponding phenylenediamine. With the tetrachloro substituted in the ring 1,4-benzoquinonediimine and the corresponding semiquinoid derivative only reduction is observed.

Activated Sterically Strained C=N Bond in N-Arylsulfonyl-p-quinonemono- and -diimines. I. Reactions with Alcohols

Analysis of the C=N-X bond angle and the energy of activation for inversion at the nitrogen atom in N-substituted p-quinonemono- and -diimines,as well of spectral parameters of N-arylsulfonyl-p-quinonemono- and -diimines with two bulky substituents in the ortho position with respect to the C=N double bond, allowed us to assume that the C=N bond in the latter qualitatively differs from that in other N-arylsulfonyl-p-quinonemono- and diimines.The presence of such activated sterically strained C=N bond favors 1,2-addition of alcohols to N-arylsulfonyl-p-benzo(naphtho)quinonemono- and -diimines with formation of 2,3,5,6-tetrachloro-4-arylsulfonylamino-4-alkoxy-2,5-cyclohexadien-1-ones, 2,3-dichloro-4-arylsulfonylamino-4-alkoxy-1,4-dihydronaphthalen-1-ones and 2,3,5,6-tetrachloro-1,4-bis-(arylsulfonylamino)-1,4-dialkoxy-2,5-cyclohexadienes.

Some Reactions of 3,6-Bis(arylsulfonylimino)-1,2,4,4,5,5-hexachlorocyclohexenes

Reduction of 3,6-bis(arylsulfonylimino)-1,2,4,4,5,5-hexachlorocyclohexenes with Zn in CH3COOH or Na2S2O4 results in elimination of two chlorine atoms to give a benzoid structure.A similar effect is produced by dialkyl hydrogen phosphites.Reactions of the title compounds with methanol and primary aromatic amines result in 1,2-addition.Treatment with secondary amines leads to nucleophilic substitution of chlorine at the sp2-hybridized carbon atom.Reactions with trimethylsilyl dialkyl phosphites proceed in two directions: elimination of two chlorine atoms and 1,6-addition followed by hydrolysis of the intermediate adduct.

CHLORINATION OF N,N'-BISARYLSULFONYL-1,4-PHENYLENEDIAMINES AND N,N'-BISARYLSULFONYL-1,4-BENZOQUINONE DIIMINES

The chlorination of N,N'-bisarylsulfonyl-1,4-phenylenediamines leads to 1,4-bisarylsulfonylimino-2,3,5,5,6,6-hexachloro-2-cyclohexenes.Together with the chlorination products chloranil and/or 2,3,5,5,6,6-hexachloro-1,2-cyclohexene-1,4-dione were isolated as a result of the competing hydrolysis process.