2654-68-4Relevant academic research and scientific papers
Paired electrochemical conversion of nitroarenes to sulfonamides, diarylsulfones and bis(arylsulfonyl)aminophenols
Mokhtari, Banafsheh,Nematollahi, Davood,Salehzadeh, Hamid
, p. 1499 - 1505 (2018/04/12)
A paired electrochemical method using nitrobenzene (NB) derivatives and arylsulfinic acids (ASAs) as starting materials was developed for the synthesis of some new sulfonamides, diarylsulfones and bis(arylsulfonyl)aminophenols. The synthetic strategy was designed using the data provided by electrochemical studies involving cyclic voltammetry on NB oxidation in the absence and presence of ASAs. The reactions have been successfully performed in an undivided cell, at carbon rod electrodes, in aqueous solutions, by constant current electrolysis at room temperature. This strategy does not require catalysts, toxic solvents and challenging workups. It is also applicable for a wide range of nitroarenes.
Reaction of semiquinoid compounds derived from N-arylsulfonyl-p-quinonemono- and diimines with tosylhydrazine
Avdeenko,Zhukova
, p. 816 - 819 (2007/10/03)
Reaction of 4-arylsulfonylimino-2,3,5,6,6-pentachloro-2-cyclohexen-1-ones with tosylhydrazine gives rise to N-arylsulfonyl-N-p-tolylsulfonyl-2,3,5,6-tetrachloroaminophenols. With 4-arylsulfonylimino-2,2,3-trichloro-1,2,3,4-tetrahydronaphthalen-1-ones and 4-arylsulfonylimino-2-dihalo-1,2,3,4-tetrahydronaphthalen-1-ones reaction products are 4-arylsulfonylamido-2,3-dichloro-4-p-tolylsulfonylhydrazido-1,4-dihydronaphthalen-1-ones and 2-p-tolylsulfonyl-1,4-naphthoquinone-4-diazide respectively. First stage of the processes consists in dehydrohalogenation yielding the corresponding N-arylsulfonyl-p-quinonimines.
Some reactions of new semiquinoid compounds derived from N-arylsulfonyl-p-quinonimines
Avdeenko,Zhukova
, p. 1482 - 1489 (2007/10/03)
Polyhalogenated semiquinoid compounds on the basis of N-arylsulfonyl-p-quinonimines react with reducing agents (zinc or sodium dithionite in acetic acid) with elimination of one or two hydrogen halide molecules, depending on the number of hydrogens at the sp3-hybridized carbon atoms, to give the corresponding benzoid structures. Dehydrohalogenation of the title compounds in chloroform in the presence of triethylamine leads to formation of quinonimines. N,N′-Bis(arylsulfonyl)-p-quinonediimine derivatives do not undergo dehydrohalogenation. Reactions with dialkyl hydrogen phosphites result mostly in 1,2-addition and formation of phosphorylated products; the reaction is likely to involve intermediate dehydrohalogenation to the corresponding quinonimines which can be isolated in the pure state.
Bromination of N,N'-Bis(arylsulfonyl)-1,4-benzoquinonediimines and 1,4-Phenylenediamines
Avdeenko, A. P.,Velichko, N. V.
, p. 221 - 225 (2007/10/02)
Depending on the solvent, molar reactant ratio, and other conditions, bromination of N,N'-bis(arylsulfonyl)-1,4-benzoquinonediimines and N,N'-bis(arylsulfonyl)-1,4-phenylenediamines yields 1,4-bis(arylsulfonylimino)-5,6-dibromo-2-cyclohexenes, N,N'-bis(ar
CHLORINATION OF N,N'-BISARYLSULFONYL-1,4-PHENYLENEDIAMINES AND N,N'-BISARYLSULFONYL-1,4-BENZOQUINONE DIIMINES
Avdeenko, A. P.,Velichko, N. V.,Tolmachev, A. A.,Pirozhenko, V. V.,Romanenko, E. A.
, p. 146 - 154 (2007/10/02)
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.
HYDROBROMINATION OF N-ARYLSULFONYL-1,4-BENZO(NAPHTHO)QUINONE MONO- AND DIIMINES
Avdeenko, A. P.,Velichko, N. V.
, p. 986 - 991 (2007/10/02)
The hydrobromination of N-arylsulfonyl-1,4-benzo(naphtho)quinone monoimines led to 2-bromo-4-arenesulfonamidophenols (or the corresponding 1-naphthols) and 2,6-dibromo-4-arenesulfonamidophenols.Their oxidation gave N-arylsulfonyl-2-bromo-1,4-benzo(naphtho
