158527-33-4Relevant academic research and scientific papers
Reactions of 2,3,5,6-tetrachloro-N-arylsulfenyl-1,4-benzoquinonimines with arenesulfinic acids
Avdeenko,Yusina,Dementii
, p. 1500 - 1503 (2007/10/03)
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.
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.
SOME REACTIONS OF 4-ARYLSULFONYLIMINO-2,3,5,5,6,6-HEXACHLORO-2-CYCLOHEXEN-1-ONES
Avdeenko, A. P.,Yusina, A. L.
, p. 1157 - 1163 (2007/10/02)
It was shown by the reactions of 4-arylsulfonylimino-2,3,5,5,6,6-hexachloro-2-cyclohexen-1-ones with reducing agents (zinc in acetic acid, Na2S2O4, Alk2POH), alcohols, aromatic amines, morpholine, and piperidine that these compounds have chemical characteristics that distinguish them both from quinonoid compounds and from systems consisting of three conjugated bonds.
