76165-36-1

Upstream product

• 76165-53-2 2,3,5,6-tetrachloro-N,N'-ditosyl-p-phenylenediamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 98472-75-4 N,N'-bis-p-chlorobenzenesulfonyl-2-chloro-1,4-phenylenediamine 
• 2654-68-4 4-chloro-N-(4-(((4-chlorophenyl)sulfonyl)amino)phenyl)benzenesulfonamide 
• 2654-77-5 N,N′-(cyclohexa-2,5-diene-1,4-diylidene)bis-(4-chlorobenzenesulfonamide) 
• 41595-29-3 N,N'-ditosyl-p-phenylenediamine 
• 106-50-3 1,4-phenylenediamine 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 624-18-0 benzene-1,4-diamine hydrochloride 

Downstream Products

• 76165-53-2 2,3,5,6-tetrachloro-N,N'-ditosyl-p-phenylenediamine 
• 173097-12-6 2,3,5,5,6,6-Hexachloro-1,4-di-p-tolylsulfonylimino-2-cyclohexene 

Relevant academic research and scientific papers

Activated Sterically Strained C=N Bond in N-Arylsulfonyl-p-quinone Mono and Diimines. III * Reaction with Hydrogen Azide

N-Arylsulfonyl-1,4-benzoquinonimines with unoccupied ortho-position with respect to carbonyl group react with HN3 at room temperature mostly by 1,4-addition; with chlorine substituents in the respective positions of the substrate reaction under heating affords products of the nucleophilic substitution. N-Arylsulfonyl-1,4-benzoquinonimines with activated sterically strained C=N bond (hereinafter acivated C=N bond) and with chlorine atoms in ortho-positions with respect to carbonyl group yield with HN3 at no heating products of 1,2-addition, and at heating both chlorines suffer nucleophilic substitution. Structurally similar N-arylsulfonyl-1,4-naphthoquinonimines react with HN3 like benzoquinonimines. In N,N′-arylsulfonyl-1,4-benzoquinonedimines with activated C=N bond 1,2-addition occurs either at one C=N bond or at both. 2-Azido-4-arylsulfonylamido(1-naphthols)phenols by intramolecular oxydation-reduction are converted into the corresponding quinonimines 2-aminosubstituted in the quinone ring. We were the first to observe C4-C2 migration of azido group simultaneously with nucleophilic substitution of chlorine in 4-azido-4-arylsulfonyl-amido-3,5-dimethyl-2,6-dichloro-(2,3,5,6-tetrachloro)-2, 5-cyclohexadiene-1-ones.

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.