50389-12-3

Upstream product

• 71-23-8 propan-1-ol 
• 39538-52-8 2,3,5,6-tetrachloro-N,N¹-bisphenylsulfonyl-p-benzoquinone diimine 
• 64-17-5 ethanol 
• 39538-52-8 N,N'-Diphenylsulfonyl-2,3,5,6-tetrachloro-1,4-benzoquinonediimine 
• 321577-37-1 N,N'-(trichloro-p-phenylene)-bis-benzenesulfonamide 
• 73021-82-6 N,N'-(trichloro-cyclohexa-2,5-diene-1,4-diylidene)-bis-benzenesulfonamide 
• 1050-82-4 N,N'-bis(phenylsulfonyl)-p-benzoquinone diimine 

Downstream Products

• 251645-37-1 C₁₈H₁₀Cl₆N₂O₄S₂ 

Relevant academic research and scientific papers

Reaction of semiquinoid compounds derived from N-arylsulfonyl-p-quinonemono- and diimines with tosylhydrazine

Reaction of 4-arylsulfonylimino-2,3,5,6,6-pentachloro-2-cyclohexen-1-ones with tosylhydrazine gives rise to N-arylsulfonyl-N-p-tolylsulfonyl-2,3,5,6-tetrachloroaminophenols. With 4-arylsulfonylimino-2,2,3-trichloro-1,2,3,4-tetrahydronaphthalen-1-ones and 4-arylsulfonylimino-2-dihalo-1,2,3,4-tetrahydronaphthalen-1-ones reaction products are 4-arylsulfonylamido-2,3-dichloro-4-p-tolylsulfonylhydrazido-1,4-dihydronaphthalen-1-ones and 2-p-tolylsulfonyl-1,4-naphthoquinone-4-diazide respectively. First stage of the processes consists in dehydrohalogenation yielding the corresponding N-arylsulfonyl-p-quinonimines.

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.

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.

REACTIONS OF N-ARYLSULFONYLQUINONE IMINES WITH ACYLHYDRAZINES

Possible directions for the reaction of N-arylsulfonylquinone imines with acylhydrazines are discussed.Reduction occurs in quinone imines with high redox potentials and hydrazines with high basicity.Otherwise either addition-elimination occurs at the C=N