216066-41-0Relevant academic research and scientific papers
Reaction of N-arylsulfonyl-p-quinonimines with hydrazoic acid
Avdeenko,Zhukova
, p. 1011 - 1013 (2007/10/03)
4-Arylsulfonylimino-2,2,3-trichloro-1,2,3,4-tetrahydronaphthalen-1-ones and 4-arylsulfonylimino-2,3-dihalo-1,2,3,4-tetrahydronaphthalen-1-ones react with hydrazoic acid to give initially products of regio-selective dehydrohalogenation. The halogen atom in position 2 of N-arylsulfonyl-1,4-naphthoquinonimines thus formed is then replaced by azido group. Reactions of 1,4-bis(arylsulfonylimino)-5,6-dibromo-2-cyclohexenes with hydrazoic acid result in formation of N,N′-bis(arylsulfonyl)-2,6-diazido-1,4-phenylenediamines.
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.
