Regiodivergent Aromatic Electrophilic Substitution Using Nitrosoarenes in Hexafluoroisopropanol: A Gateway for Diarylamines and p-Iminoquinones Synthesis
A metal-free aromatic electrophilic substitution reaction using nitrosoarenes as the electrophile in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) is reported. HFIP activates nitrosoarene towards the electrophilic C?H amination followed by a concomitant N?O bo
Oximation of 2-(R1-Amino)-4-(R2-imino)naphthalen-1(4H)-ones
The oximation of 2-(R1-amino)-4-(R2-imino)naphthalen-1(4H)-ones with hydroxylamine hydrochloride in pyridine afforded 2-(R-amino)-4-(hydroxyimino)naphthalen-1(4H)-ones.
Gornostaev,Rukovets,Arnold,Khalyavina, Yu. G.,Gatilov, Yu. V.
p. 78 - 86
(2018/06/15)
RESEARCH IN THE CHEMISTRY OF HETEROCYCLIC QUINONE IMINES. 11. EFFECT OF BENZANNELATION ON THE OXIDATIVE CYCLIZATION OF DIARYLAMINO-N-ARYL-1,4-BENZOQUINONE MONOIMINES TO PHENAZINONE DERIVATIVES
2,5-Diarylamino-N-α(β)-naphthyl-1,4-benzoquinone monoimines undergo oxidative cyclization to give benzannelated phenazinone derivatives.The effect of an N-aryl fragment on the ease of cyclization decreases in the order N-β-naphthyl > N-α-naphthyl > N-phenyl. 2-Arylamino-N-phenyl-1,4-naphthoquinone monoimines do not undergo oxidative cyclization to phenazinones.
Afanas'eva, G. B.,Tsoi, E. V.
p. 616 - 620
(2007/10/02)
Nitroxide Radicals. Part 21. Spontaneous Decomposition of N-Aryl 1- and 2-Naphthyl Nitroxides
N-Aryl 1-naphthyl nitroxides self-react in solution to give the corresponding secondary amines and N-aryl-1,4-naphthoquinone imines.When reaction at the 4-naphthyl position is hindered by substituents benzoquinone imines are also produced.N-Phenyl 2-naphthyl nitroxide under similar conditions gives the corresponding amine and 2-phenylamino-1,4-naphthoquinone via a 1,2-naphthoquinone imine N-oxide intermediate.
Forrester, Alexander R.,Fullerton, Joseph D.,McConnachie, Gordon
p. 1759 - 1764
(2007/10/02)
Reactivity and Structure of N-Phenyl-1-naphthylamines and Related Compounds. Part 3. Reaction with Oxygen-centred Radicals
Comparison is made between products obtained by oxidation of N-phenyl-1-naphthylamines and 1-naphthyl phenyl nitroxides with peroxyl radicals.It is concluded that oxidation of the amines does not proceed to a considerable extent via the nitroxides.Comparison is also made of products obtained from these amines and nitroxides by oxidation with Fremy's salt.
Forrester, Alexander R.,Fullerton, Joseph D.,McConnachie, Gordon
p. 2711 - 2715
(2007/10/02)
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