14034-15-2

Upstream product

• 15980-22-0 3,5-dimethyl-4-hydroxyaniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 14034-17-4 2,6-Dimethyl-N-(p-tosyl)-p-benzochinonimin-⁽⁴⁾ 
• 527-61-7 2,6-dimethyl-1,4-benzoquinone 
• 576-26-1 2.6-dimethylphenol 
• 108-68-9 3,5-Dimethylphenol 

Downstream Products

• 14034-17-4 2,6-Dimethyl-N-(p-tosyl)-p-benzochinonimin-⁽⁴⁾ 

Relevant academic research and scientific papers

Reaction of N-sulfonyl derivatives of 1,4-benzoquinone monoimine with substituted hydrazines

Reaction direction of N-sulfonyl derivatives of 1,4-benzoquinone monoimine with substituted hydrazines depends on the redox potential of the quinone imine and on the basicity of the hydrazine. Aryl (alkyl)hydrazines of high basicity favor the reduction of

The Diels-Alder reactions of para-benzoquinone nitrogen-derivatives: An experimental and theoretical study

An experimental and theoretical study of the comparative reactivity and selectivity of the Diels-Alder reactions of para-benzoquinones and three nitrogen derivatives have been performed. The mono-oximes derivatives do not react under the tested reaction conditions, whereas the tosylated mono-oximes react slowly. However, the mono N-tosyl imines show excellent reactivity, and superior to the parent parabenzoquinones. DFT calculations support these experimental results.

Thiocyanation of N-arylsulfonyl-, N-aroyl-, and N-[(N-arylsulfonyl) benzimidoyl]-1,4-benzoquinone imines

Reactions of thiocyanate ion with N-aroyl-, N-arylsulfonyl-, and N-(N-arylsulfonylbenzimidoyl)-1,4-benzoquinone imines follow the 1,4-addition pattern, and the adducts undergo intramolecular cyclization to give the corresponding N-substituted 5-amino-1,3-

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.