- The kinetics of the reversible chain reaction between 2,5-dichloroquinone and 4-hydroxydiphenylamine
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The paper presents the results obtained in a study of the kinetics of the reversible chain reaction between 2,5-dichloroquinone and 4-hydroxydiphenylamine (K eq = 3.2). We studied the dependence of the reaction rate on the concentrations of the initiator, initial reagents, and all products. The equations obtained earlier for the rate of reversible chain reactions and the method of equal concentrations suggested in this work were used to estimate the rate constants of most of the reaction mechanism elementary steps from the experimental data. The results obtained were shown to closely agree with and agument the data obtained earlier for the kinetics of the chain reaction between N-phenyl-1,4-benzoquinonemonoimine and 2,5-dichlorohydroquinone. On the whole, all the elementary steps of these two (forward and back) reversible chain reactions were characterized by rate constant values.
- Antonov,Varlamov
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Read Online
- Palladium-catalyzed carbonylation of iminoquinones and aryl iodides to access arylp-amino benzoates
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A palladium-catalyzed carbonylation of iminoquinones and aryl iodides has been developed for the construction of arylp-amino benzoates. Using benzene-1,3,5-triyl triformate (TFBen) as the CO source, the reaction proceeded well to give various arylp-amino benzoates in good to excellent yields. Additionally, control experiments were conducted to gain more insights into the reaction mechanism.
- Wang, Siqi,Wu, Xiao-Feng,Yao, Lingyun,Ying, Jun
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supporting information
p. 8246 - 8249
(2021/10/12)
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- Copper-Catalyzed Aqueous N?O Bond Cleavage of 2-Oxa-3-Azabicyclo Compounds to Cyclic cis-1,4-Amino Alcohols
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The N?O bond cleavage of 2-oxa-3-azabicyclo substrates, which are readily prepared by the hetero Diels-Alder reaction between nitroso dienophiles and cyclic 1,3-dienes, was effectively catalyzed by heterogeneous copper-on-carbon (Cu/C) under aqueous condi
- Yasukawa, Naoki,Miki, Yuya,Kuwata, Marina,Sajiki, Hironao,Sawama, Yoshinari
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p. 5632 - 5637
(2020/09/11)
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- Pd-Catalyzed Redox-Neutral C-N Coupling Reaction of Iminoquinones with Electron-Deficient Alkenes without External Oxidants: Access of Tertiary (E)-Enamines and Application to the Synthesis of Indoles and Quinolin-4-ones
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A novel and efficient reductive N-alkenylation of iminoquinones with electron-deficient olefins has been successfully developed by Pd(II)-catalyzed redox-neutral reactions, which provides a synthesis of tertiary (E)-enamines. We further demonstrate that the tertiary enamines can be converted to multifarious N-heterocyclic compounds, indoles, and quinolones in good yields.
- Jillella, Raveendra,Raju, Selvam,Hsiao, Huan-Chang,Hsu, Day-Shin,Chuang, Shih-Ching
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supporting information
p. 6252 - 6256
(2020/08/12)
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- Method for synthesizing p-phenylquinone monoimide through p-aminophenol
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The invention discloses a method for synthesizing p-phenylquinone monoimide through p-aminophenol. The method comprises the steps that by means of a one-step method, p-aminophenol is directly adoptedto coupled with phenylboronic acid for dehydrogenation o
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Paragraph 0031-0046
(2019/07/08)
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- A new method for the synthesis of iminoquinones via DMP-mediated oxidative reaction
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Iminoquinones were synthesized by oxidation of primary and secondary amines with hypervalent iodine reagent Dess-Martin periodinane in average to good yields, and possible mechanisms were postulated. This methodology is convenient to establish a library of diversified iminoquinone compounds and has great significance for their potential application in the field of pharmaceuticals.
- Ma, Hengchang,Wu, Shang,Sun, Qiangsheng,Li, Hongyan,Chen, Yannan,Zhao, Wenqing,Ma, Bihui,Guo, Qing,Lei, Ziqiang,Yan, Jun
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experimental part
p. 3295 - 3300
(2010/11/20)
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- Rate constants of elementary steps of the reversible chain reaction of N-phenyl-1,4-benzoquinonemonoimine with 2,5-dichlorohydroquinone
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The kinetics of reversible chain reactions in quinoneimine-hydroquinone systems has first been studied for the reaction of N-phenyl-1,4- benzoquinonemonoimine with 2,5-dichloro-hydroquinone used as an example. The dependences of the reaction rate on the concentration of the initial reactants, initiator, and each product were studied. The reliable estimates of the rate constants of 11 (of 12) elementary steps of this reaction were obtained from the experimental data using the earlier derived formulas and the method of equal concentrations developed in the present work.
- Antonov,Varlamov
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p. 883 - 889
(2008/09/18)
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- Determination of dissociation energies of N-H bond in the 4-anilinodiphenylaminyl radical and O-H bond in the 2,5-dichloro-4- hydroxyphenoxyl radical from the equilibrium constants of chain reactions in quinoneimine-hydroquinone systems
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The temperature dependences of the equilibrium constants of two chain reversible reactions in quinonediimine (quinonemonoimine)-2,5- dichlorohydroquinone systems in chlorobenzene were studied. The enthalpy of equilibrium of the reversible reaction of quinonediimine with 4-hydroxydiphenylamine was estimated from these data (ΔH = - 14.4±1.6 kJ mol-1) and a more accurate value of the N-H bond dissociation energy in the 4-anilinodiphenylaminyl radical was determined (DNH = 278.6±3.0 kJ mol-1). A chain mechanism was proposed for the reaction between quinonediimine and 2,5-dichlorohydroquinone, and the chain length was estimated (ν = 300 units) at room temperature. Processing of published data on the rate constant of the reaction of styrylperoxy radicals with 2,5-dichlorohydroquinone in the framework of the intersecting parabolas method gave the O-H bond dissociation energy in 2,5-dichlorohydroquinone: DOH = 362.4±0.9 kJ mol-1. Taking into account these data, the O-H bond dissociation energy in the 2,5-dichlorosemiquinone radical was found: DOH = 253.6±1.9 kJ mol-1.
- Antonov,Gadomsky,Varlamov
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p. 1723 - 1728
(2008/02/09)
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- Influence of the acidity on the kinetics of diphenylamine oxidation by peroxodisulfate anions
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A kinetic study is reported on the oxidation of diphenylamine (DPA) by peroxodisulfate (PDS) anions in H2SO4 and buffered acetic acid - acetate 20percent v/v methanol-water media.The primary detectable product of the reaction is N-phenyl-p-benzoquinoneimi
- Balon, M.,Guardado, P.,Carmona, C.,Hidalgo, J.,Munoz, M. A.
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p. 167 - 174
(2007/10/02)
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- Catalytic oxidation of hydroxy containing aromatic compounds
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The present invention relates to a process for the catalytic oxidation of hydroxy containing aromatic compounds to form the respective quinone compounds comprising contacting a hydroxy containing aromatic compound of the formula: STR1 with a molecular oxy
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- Dye-sensitized photooxygenation of diphenylamine in sodium dodecyl sulphate micellar solution
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A kinetic study of methylene blue (MB) sensitized photooxygenation of diphenylamine (DPA) in sodium dodecyl sulphate micellar solution has been shown to give N-phenyl-p-benzoquinoneimine (PBQ) as the only primary coloured product.The steady state rate exp
- Dahmiwal, N. R.,Grewal, Daisy
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p. 660 - 664
(2007/10/02)
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- Mechanistic Features of Hexacyanoferrate(III) Oxidation of Diphenylamine in Alkaline Medium
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Oxidation of diphenylamine (DPA) by hexacyanoferrate(III) in alkaline medium gives two products identified as N-phenyl-p-benzoquinoneimine (PBQ) and hexacyanoferrate(II); the stoichiometric ratio being / = 3.9.The pseudo-second order rate co
- Sidhu, K. S.,Bansal, W. R.,Kaur, Sukhjeet
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p. 740 - 748
(2007/10/02)
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- Chlorophyll Sensitized Photo-oxidation of Diphenylamine
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Chlorophyll sensitized oxidation of diphenylamine in the presence of oxygen yields N-phenyl-p-benzoquinonimine as isolable and primary product and not diphenylnitrogen radical reported earlier by Russian workers .The ph
- Kumar, Ravinder,Bansal, W. R.,Sidhu, K. S.
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p. 373 - 376
(2007/10/02)
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