216066-10-3

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 3096-70-6 3,5-dimethyl-4-aminophenol 

Downstream Products

• 216066-11-4 N-(3-azido-4-hydroxy-2,6-dimethyl-phenyl)-benzenesulfonamide 
• 1343489-75-7 C₂₀H₂₅N₃O₃S 
• 1338060-27-7 ethyl 5-[(benzenesulfonyl)amino]-2,4,6-trimethyl-1-benzofuran-3-carboxylate 
• 1338060-26-6 N-(3-acetyl-2,4,6-trimethyl-1-benzofuran-5-yl)-benzenesulfonamide 
• 1385823-78-8 N-(2,6-dimethyl-4-oxo-1-cyclohexyloxycyclohexa-2,5-dien-1-yl)benzenesulfonamide 
• 216066-19-2 N-(3-azido-5-chloro-4-hydroxy-2,6-dimethyl-phenyl)-benzenesulfonamide 
• 216066-26-1 N-(1-azido-3,5-dichloro-2,6-dimethyl-4-oxo-cyclohexa-2,5-dienyl)-benzenesulfonamide 
• 321687-62-1 4-phenylsulfonylamido-3,5-dimethyl-2,6-dichlorophenol 
• 216066-21-6 N-(3-azido-5-chloro-2,6-dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-benzenesulfonamide 
• 216066-24-9 N-phenylsulfonyl-3,5-dimethyl-2,6-dichloro-1,4-benzoquinone monoimine 
• 216066-17-0 N-(3-chloro-2,6-dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis of 5-substituted 2,3-dihydrobenzofurans in a one-pot oxidation/cyclization reaction

Variously substituted 2,3-dihydrobenzofurans have been synthesized according to a sequential one-pot oxidation/cyclization procedure between para-aminophenol derivatives and an azadiene.

Activated sterically strained C=N bond in N-arylsulfonyl-p-quinonemono- and diimines: VII. 1H and 13C NMR spectra of N-arylsulfonyl-p-benzoquinonemono and diimines

In the N-arylsulfonyl-2,3,5,6-tetrachloro-1,4-benzoquinonemono- and diimines and in the N-arylsulfonyl-3,5-dimethyl-1,4-benzoquinonemonoimines the inversion around C=N bond occurs with high rate due to increased bond angle C=N-S, i.e. to the presence of a sterically strained C=N bond. In the N-arylsulfonyl-2,6-dimethyl-1,4-quinonemonoimines where the C=N bond is not sterically strained occurs degenerate Z,E-isomerization. 5-Methoxy-N-phenylsulfonyl-3-chloro-1,4-benzoquinonimine with no sterically strained C=N bond due to the free rotation of the methoxy group exists in solution as E-isomer with respect to chlorine.

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.