The Effect of Acylamino Groups in Diazo-coupling Reactions
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概要
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A kinetic study has been made of the coupling reactions of diazonium salts with <I>N</I>,<I>N</I>-dialkyl-<I>N</I>′-acyl-<I>m</I>-phenylenediamines, including <I>N</I>′-acetyl- (I,II), <I>N</I>′-benzoyl- (III), <I>N</I>′-carboethoxy- (IV), and <I>N</I>′-<I>p</I>-toluene-sulfonyl derivatives (V, VI). It was found from the pH dependence of the apparent rate constant that the reactive species of a substrate varies with the pH of the medium, from an undissociated molecule to an anion formed by the ionization of an acylamino group. In the case of I, the activating effect of the dissociated acylamino group seems to be higher than that of the undissociated acylamino group by some 8 powers of ten.
- 公益社団法人 日本化学会の論文
著者
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Hashida Yoji
Department of Chemistry, Faculty of Engineering, Gunma University
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Sekiguchi Shizen
Department of Chemistry, Faculty of Engineering, Gunma University
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Matsui Kohji
Department of Chemistry, Faculty of Engineering, Gunma University
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Mitsumura Kazuo
Department of Chemistry, Faculty of Engineering, Gunma University
関連論文
- Phase-transfer-catalyzed azo coupling reactions in two-phase systems.
- Photochemical reactions of azidotriazines with aromatic substrates.
- Solvent Effects in Diazo-coupling Reactions
- Rearrangement of 2-Aryloxybenzazoles
- Tris(benzimidazo)-1,3,5-triazine from the Thermolysis of 2-Aryloxybenzimidazoles
- Studies of Azo Colors. VIII. The Azo-coupling Reactions of Active Methylene Compounds
- Aromatic nucleophilic substitution. XVII. Formation and decomposition of anionic .SIGMA. complexes in reactions of 2-acetylaminoethyl 2,6-dinitrophenyl ether and N-acetyl-N-(2-hydroxyethyl)-2,6-dinitroaniline with potassium t-butoxide.
- Derivatives of Ditriazinylamine
- Photolyses of azidotriazines in organic nitro compounds.
- Aromatic nucleophilic substitution. XIII. Confirmation of the anionic .SIGMA. complexes in the reactions of 2,4-dinitro- and 2,4,5-trinitro-1-(1-piperidyl)naphthalenes with piperidine in dimethyl sulfoxide.
- Reactions of Diazomethyl-1,3,5-triazines with Cyclohexane
- The Effect of Acylamino Groups in Diazo-coupling Reactions
- Effects of Substituents on the Smiles Rearrangement of O-s-Triazmyl-2-aminophenoIs
- Aromatic nucleophilic substitution. VII. Electronic structure of 1,1-disubstituted 2,4-dinitronaphthalene Meisenheimer complexes.
- The Photochemical Rearrangements of N-Acetyl Diphenylamine and N-Acetyl Carbazole
- Ring-opening reactions of cyclic ethers. IX. Molecular weight distribution of adducts in the acid- catalyzed reactions of epichlorohydrin with alcohols.
- The Diazo-coupling Reaction of Phenol in Organic Solvents. The Isomer Ratio
- Effects of N-Acyl- and N-s-Triazinyl Groups on the Rearrangement of S-(s-Triazinyl)-2-aminothiophenols and O-(s-Triazinyl)-2-aminophenols
- Studies of Azo Colors. XI. The Diazo-coupling Reaction of Pyrroles
- Aromatic nucleophilic substitution. XV. Stopped-flow kinetics of the formation and decomposition of 1,3- and 1,1-disubstituted Meisenheimer complexes in the reactions of 1-dialkylamino-2,4-dinitronaphthalenes with potassium methoxide in dimethyl sulfoxide
- The Catalytic Effect of Acid on the O→N Migration of the s-Triazinyl Group of O-(s-Triazinyl)-2-aminophenols
- Aromatic Nulceophilic Substitution. I. Preparation of Spiro Meisenheimer Complexes of Arenes
- Diazotization of aromatic primary amines of weak basicity. II. Reduction of arenediazonium salts with alkylbenzene derivatives.
- The Activating Effects of Amino Groups in Diazo-coupling Reactions
- Aromatic nucleophilic substitution. XVIII. Kinetics of reactions of 2-(acetylamino)ethyl 2,6-dinitrophenyl ether and N-acetyl-N-(2-hydroxyethyl)-2,6-dinitroaniline with sodium isopropoxide.
- Photochemical reactions of N-acyl-2,3-dihydrobenzoxazol-2-ones.
- Complexation of arenediazonium ions with a macrocyclic polyether. The stability constants for the complexes.
- Aromatic nucleophilic substitution. 25. Stopped-flow kinetics of reactions of 1-ethoxy-2,4-dinitronaphthalene with pyrrolidine and piperidine in dimethyl sulfoxide solution.
- Reactions of azoxybenzene with dichlorocarbene in the phase-transfer-catalyzed system.
- N2→N1 Migration of s-Triazinyl Group in the Reaction of N-Acetyl-N2-(s-triazinyl)alkylenediamines
- Aromatic Nitration. II. Competitive Nitration of Toluene and Benzene in Organic Solvents
- The reactions of 2-substituted 4-chloro-6-(2-hydroxy-1-naphthyl)-1,3,5-triazines with several nucleophiles.
- The Catalytic Effect of Bases on the O→N Migration of the s-Triazinyl Group in O-(s-Triazinyl)-2-aminophenols
- Aromatic nucleophilic substitution. XVI. Stopped-flow kinetics of formation and decomposition of 1,3- and 1,1-disubstituted anionic .SIGMA. complexes in reactions of 1-dimethylamino-2,4-dinitronaphthalene with potassium alkoxides in dimethyl sulfoxide-alc
- Aromatic nucleophilic substitution. 24. Stopped-flow kinetics of the formation and decomposition of 2,4- and 4,4-disubstituted Meisenheimer complexes in the reaction of 4-piperidino-1,3-dinitrophenanthrene with potassium methoxide in dimethyl sulfoxide-me
- Reaction of azobenzene with dichlorocarbene in phase-transfer-catalyzed system.
- Ring-opening Reactions of Cyclic Ethers. VIII. Acid-catalyzed Ring-opening Reactions of Isobutylene Oxide in Alcohols
- The N1→N2 Migration of the s-Triazinyl Group of 4-Substituted N1,N1-Bis-(s-triazinyl)-o-phenylenediamines