14034-17-4Relevant academic research and scientific papers
The Diels-Alder reactions of para-benzoquinone nitrogen-derivatives: An experimental and theoretical study
Uliana, Marciana P.,Servilha, Bruno M.,Alexopoulos, Olga,De Oliveira, Kleber T.,Tormena, Cláudio F.,Ferreira, Marco A.B.,Brocksom, Timothy J.
, p. 6963 - 6973 (2015/11/09)
An experimental and theoretical study of the comparative reactivity and selectivity of the Diels-Alder reactions of para-benzoquinones and three nitrogen derivatives have been performed. The mono-oximes derivatives do not react under the tested reaction conditions, whereas the tosylated mono-oximes react slowly. However, the mono N-tosyl imines show excellent reactivity, and superior to the parent parabenzoquinones. DFT calculations support these experimental results.
Thiocyanation of N-arylsulfonyl-, N-aroyl-, and N-[(N-arylsulfonyl) benzimidoyl]-1,4-benzoquinone imines
Avdeenko,Pirozhenko,Konovalov,Roman'Kov,Palamarchuk,Shishkinc
experimental part, p. 408 - 416 (2009/09/06)
Reactions of thiocyanate ion with N-aroyl-, N-arylsulfonyl-, and N-(N-arylsulfonylbenzimidoyl)-1,4-benzoquinone imines follow the 1,4-addition pattern, and the adducts undergo intramolecular cyclization to give the corresponding N-substituted 5-amino-1,3-
Activated sterically strained C=N bond in N-arylsulfonyl-p-quinonemono- and diimines: VII. 1H and 13C NMR spectra of N-arylsulfonyl-p-benzoquinonemono and diimines
Avdeenko
, p. 522 - 527 (2007/10/03)
In the N-arylsulfonyl-2,3,5,6-tetrachloro-1,4-benzoquinonemono- and diimines and in the N-arylsulfonyl-3,5-dimethyl-1,4-benzoquinonemonoimines the inversion around C=N bond occurs with high rate due to increased bond angle C=N-S, i.e. to the presence of a sterically strained C=N bond. In the N-arylsulfonyl-2,6-dimethyl-1,4-quinonemonoimines where the C=N bond is not sterically strained occurs degenerate Z,E-isomerization. 5-Methoxy-N-phenylsulfonyl-3-chloro-1,4-benzoquinonimine with no sterically strained C=N bond due to the free rotation of the methoxy group exists in solution as E-isomer with respect to chlorine.
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.
EFFECT OF ARENESULFONAMIDE GROUP ON THE NATURE OF SUBSTITUTION IN THE AROMATIC RING. IV. REACTION OF DERIVATIVES OF 4-SULFONAMIDOPHENOL AND 1,4-DI(SULFONAMIDO)BENZENE WITH NITROSATING AGENTS
Zakatov, V.V.,Dubina, V.L.,Torubarnov, I.V.
, p. 303 - 306 (2007/10/02)
The action of nitrosating agents on derivatives of 4-sulfonamidophenol and 1,4-di(sulfonamido)benzene leads to the formation of either the nitration products or the oxidation products.
