330212-89-0

Upstream product

• 7498-47-7 bis-(4-dimethylamino-phenyl)-hydroxyphosphine 
• 141481-36-9 2,3,5,6-Tetrachloro-N-phenylsulfonyl-1,4-benzoquinonemonoimine 
• 5471-90-9 N-(4-hydroxyphenyl)benzenesulfonamide 
• 873-55-2 sodium benzenesulfonate 
• 99323-78-1 C₁₃H₇Cl₄NOS 
• 83167-40-2 C₁₂H₅Cl₄NOS 
• 91358-28-0 C₁₂H₄Cl₄N₂O₃S 

Downstream Products

• 141481-36-9 2,3,5,6-Tetrachloro-N-phenylsulfonyl-1,4-benzoquinonemonoimine 

Relevant academic research and scientific papers

Reactions of 2,3,5,6-tetrachloro-N-arylsulfenyl-1,4-benzoquinonimines with arenesulfinic acids

Arenesulfinic acids react with 2,3,5,6-tetrachloro-N-arylsulfenyl-1,4-benzoquinonimines, following the 1,6-addition pattern. The reactions with excess arenesulfinic acid result in elimination of arenethiol and formation of 2,3,5,6-tetrachloro-4-arylsulfonylaminophenols. Oxidation of the latter yields 2,3,5,6-tetrachloro-N-arylsulfonyl-1,4-benzoquinonimines which are difficult to obtain by other methods.

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.

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-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.