76165-36-1Relevant articles and documents
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.
QUINONE IMINES AND QUINONOID MACROCYCLES IV. INVESTIGATIONS OF THE ELECTRON-ACCEPTOR PROPERTIES OF N,N'-DIBENZOYL- AND N,N'-BIS(ORGANOSULFONYL)-p-BENZOQUINONE DIIMINE DERIVATIVES
Lokmane, E. Ya.,Sarul', E. A.,Sekatsis, I. P.,Freimanis, Ya. F.,Liepin'sh, E. E.
, p. 1502 - 1507 (2007/10/02)
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