216066-24-9

Upstream product

• 3096-70-6 3,5-dimethyl-4-aminophenol 
• 98-09-9 benzenesulfonyl chloride 
• 216066-10-3 3,5-dimethyl-N-phenylsulfonyl-1,4-benzoquinonimine 
• 216066-17-0 N-(3-chloro-2,6-dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-benzenesulfonamide 
• 321687-61-0 N-(3-chloro-4-hydroxy-2,6-dimethyl-phenyl)-benzenesulfonamide 
• 303049-18-5 N-(4-hydroxy-2,6-dimethyl-phenyl)-benzenesulfonamide 
• 321687-62-1 4-phenylsulfonylamido-3,5-dimethyl-2,6-dichlorophenol 

Downstream Products

• 216066-26-1 N-(1-azido-3,5-dichloro-2,6-dimethyl-4-oxo-cyclohexa-2,5-dienyl)-benzenesulfonamide 
• 216066-21-6 N-(3-azido-5-chloro-2,6-dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-benzenesulfonamide 

Relevant academic research and scientific papers

Halogenation of N-substituted para-quinone monoimine and para-quinone monooxime esters: V. Chlorination and bromination of N-arylsulfonyl-1,4- benzoquinone monoimines dialkyl-substituted in the quinoid ring

The direction of halogen addition to N-arylsulfonyl-1,4-benzoquinone monoimines dialkyl-substituted in the quinoid ring is governed by the steric factors: the size and position of the substituent, the halogen volume, and the position of the substituent at

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.