68375-07-5Relevant academic research and scientific papers
Halogenation of N-substituted p-quinone imines and p-quinone oxime esters: IV. Chlorination and bromination of N-arylsulfonyl-2(3)-methyl(2-chloro)-1,4- benzoquinone monoimines
Avdeenko,Konovalova
, p. 349 - 364 (2007/10/03)
The addition of halogens to N-arylsulfonyl-1,4-benzoquinone imines, which exist in a solution as Z and E isomers, is controlled by the steric factor. Z-E Isomerization strongly affects the stability of cyclohexene structures formed by halogenation of 1,4-
Chlorination of N-(N-arylsulfonylarylimidoyl)-1,4-benzoquinone imines and their reduced forms
Avdeenko,Marchenko,Konovalova
, p. 546 - 552 (2007/10/03)
The study of chlorination of N-(N-arylsulfonylarylimidoyl)-1, 4-benzoquinone imines and of N-(N-arylsulfonylarylimidoyl)-1,4-aminophenols revealed that the dominant stage in the process was the formation of cyclohexene structures, 4-(N-arylsulfonylarylimidoyl)imino-2,5,6-trichloro-2-cyclohexene-1-ones, resulting from addition of a Cl2 molecule across the C=C bond of the quinoid ring. These substances suffer a prototropic rearrangements yielding N-(N-arylsulfonylarylimidoyl)-2,3,6-trichloro-4-aminophenols. The latter are the most common reaction products. The products of deeper chlorination were also obtained.
Synthesis of Polyhalogenated 2-Cyclohexane-1,4-dione Derivatives Containing Hydrogen at the sp3-Carbon Atoms from N-Arylsulfonyl-p-quinonimines and N,N'-Bis(arylsulfonyl)-p-quinonediimines
Avdeenko, A. P.,Zhukova, S. A.
, p. 388 - 396 (2007/10/03)
Chlorination and bromination of N-arylsulfonyl-1,4-benzo(naphtho)quinonimines, N,N'-bis(arylsulfonyl)-1,4-benzoquinonediimines, N-arylsulfonyl-4-aminophenols, and N-arylsulfonyl-4-aminonaphthols gave a number of stable polyhalogenated structures containing hydrogen at the sp3-hybridized carbon atoms. The chlorination and bromination schemes of N-arylsulfonyl-p-quinonimines are discussed.
REACTION OF N-ARYLSULFONYL-1,4-BENZOQUINONE MONOIMINES WITH HYDROGEN CHLORIDE IN DIMETHYLFORMAMIDE
Avdeenko, A. P.,Velichko, N. V.
, p. 967 - 969 (2007/10/02)
On reacting N-arylsulfonyl-2,6-dichloro-1,4-benzoquinone monoimines with hydrogen chloride in dimethylformamide, the chlorine atom enters into the position ortho to the nitrogen atom of the arylsulfonylquinone imine.
CHLORINATION OF p-ARENESULFONAMIDOPHENOLS AND N-(ARYLSULFONYL)-p-BENZOQUINONE
Avdeenko, A. P.,Velichko, N. V.,Romanenko, E. A.,Pirozhenko, V. V.,Shurpach, V. I.
, p. 2085 - 2095 (2007/10/02)
The chlorination of p-arenesulfonamidophenols and N-(arylsulfonyl)-p-benzoquinone imines leads to 4--2,3,5,5,6,6-hexachloro-2-cyclohexen-1-ones.N-(Arylsulfonyl)-2,3,5,6-tetrachloro-p-benzoquinone imines were prepared for the first time.As a result of the occurrence of a competing hydrolysis process, in some cases, as well as chlorination products chloranil and/or 2,3,5,5,6,6-hexachloro-2-cyclohexene-1,4-dione were isolated.
