216066-25-0Relevant 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
Avdeenko,Konovalova
, p. 669 - 682 (2007/10/03)
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
Reactions of Polyhalogenated 4-Arylsulfonylimino-2-cyclohexenones and 3,6-Bis(arylsulfonylimino)cyclohexenes with Alcohols
Avdeenko, A. P.,Zhukova, S. A.
, p. 423 - 427 (2007/10/03)
Polyhalogenated 4-arylsulfonylimino-2-cylohexenones and 3,6-bis(arylsulfonylimino)cyclohexenes react with alcohols to give 1,2-addition products at the C=N bond through intermediate formation of N-arylsulfonylimino-p-quinonimines. Heating of the adducts above the melting point results in elimination of alcohol molecule and formation of quinoid structures.
Activated Sterically Strained C=N Bond in N-Arylsulfonyl-p-quinone Mono and Diimines. III * Reaction with Hydrogen Azide
Avdeenko,Menafova,Zhukova
, p. 210 - 220 (2007/10/03)
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.
