- Reaction of N-Arylsulfonyl-p-quinonimines and semiquinoid structures produced therefrom with Bis(p-dimethylaminophenyl)phosphinite
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N-Arylsulfonyl-1,4-benzoquinonemonoimines react with bis(N-dimethylaminophenyl)phosphinite in keeping with the character and position of substituents in the quinoid ring along 1,4-, 6,1-, or 1,2-addition way; N-arylsulfonyl-1,4-naphthoquinonemonoimines react along 1,4-, 6,1-, 1,2-, or 6,3-addition. Semiquinoid polyhalostructures generated therefrom react similarly to the corresponding quinonimines possessing several chlorine substituents in the quinoid ring. N,N-Diarylsulfonyl-1,4-benzoquinonediimines with no substituents in the ring yield with bis(p-dimethylaminophenyl)phosphinite 1,4-addition products. Along a competing reaction quinonediimine is reduced to the corresponding phenylenediamine. With the tetrachloro substituted in the ring 1,4-benzoquinonediimine and the corresponding semiquinoid derivative only reduction is observed.
- Avdeenko
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p. 1182 - 1190
(2007/10/03)
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- Activated Sterically Strained C=N Bond in N-Arylsulfonyl-p-quinonemono- and -diimines. I. Reactions with Alcohols
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Analysis of the C=N-X bond angle and the energy of activation for inversion at the nitrogen atom in N-substituted p-quinonemono- and -diimines,as well of spectral parameters of N-arylsulfonyl-p-quinonemono- and -diimines with two bulky substituents in the ortho position with respect to the C=N double bond, allowed us to assume that the C=N bond in the latter qualitatively differs from that in other N-arylsulfonyl-p-quinonemono- and diimines.The presence of such activated sterically strained C=N bond favors 1,2-addition of alcohols to N-arylsulfonyl-p-benzo(naphtho)quinonemono- and -diimines with formation of 2,3,5,6-tetrachloro-4-arylsulfonylamino-4-alkoxy-2,5-cyclohexadien-1-ones, 2,3-dichloro-4-arylsulfonylamino-4-alkoxy-1,4-dihydronaphthalen-1-ones and 2,3,5,6-tetrachloro-1,4-bis-(arylsulfonylamino)-1,4-dialkoxy-2,5-cyclohexadienes.
- Avdeenko, A. P.,Yusina, A. L.,Menafova, Yu. V.,Pirozhenko, V. V.
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p. 1386 - 1390
(2007/10/03)
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- Some Reactions of 3,6-Bis(arylsulfonylimino)-1,2,4,4,5,5-hexachlorocyclohexenes
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Reduction of 3,6-bis(arylsulfonylimino)-1,2,4,4,5,5-hexachlorocyclohexenes with Zn in CH3COOH or Na2S2O4 results in elimination of two chlorine atoms to give a benzoid structure.A similar effect is produced by dialkyl hydrogen phosphites.Reactions of the title compounds with methanol and primary aromatic amines result in 1,2-addition.Treatment with secondary amines leads to nucleophilic substitution of chlorine at the sp2-hybridized carbon atom.Reactions with trimethylsilyl dialkyl phosphites proceed in two directions: elimination of two chlorine atoms and 1,6-addition followed by hydrolysis of the intermediate adduct.
- Avdeenko, A. P.,Yusina, A. L.
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p. 696 - 699
(2007/10/03)
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- CHLORINATION OF N,N'-BISARYLSULFONYL-1,4-PHENYLENEDIAMINES AND N,N'-BISARYLSULFONYL-1,4-BENZOQUINONE DIIMINES
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The chlorination of N,N'-bisarylsulfonyl-1,4-phenylenediamines leads to 1,4-bisarylsulfonylimino-2,3,5,5,6,6-hexachloro-2-cyclohexenes.Together with the chlorination products chloranil and/or 2,3,5,5,6,6-hexachloro-1,2-cyclohexene-1,4-dione were isolated as a result of the competing hydrolysis process.
- Avdeenko, A. P.,Velichko, N. V.,Tolmachev, A. A.,Pirozhenko, V. V.,Romanenko, E. A.
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p. 146 - 154
(2007/10/02)
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