The reactions of 2-substituted 4-chloro-6-(2-hydroxy-1-naphthyl)-1,3,5-triazines with several nucleophiles.

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概要

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• The nucleophilic substitution reactions of 2-methoxy- and 2-diethylamino-4-chloro-6-(2-hydroxy-1-naphthyl)-1,3,5-triazines (<B>1</B>) with aniline, diethylamine, sodium azide, and sodium methoxide were carried out and compared with the reactions of the corresponding derivatives of 4-chloro-6-(4-hydroxy-1-naphthyl)-1,3,5-triazine (<B>2</B>) and 4-chloro-6-(1-naphthyl)-1,3,5-triazine (<B>3</B>). Compound <B>1</B> was found to be more reactive than the corresponding (<B>2</B>) and (<B>3</B>), not only in the reactions of a neutral molecule, but also in those of anionic species. The results of the reactions of neutral species are interpreted in terms of the difference in solvation toward the substrates; however, the loss of coplanarity between the naphthalene and triazine nuclei may be responsible for the high reactivity of Compound <B>1</B> in the reactions of anionic species.

• 公益社団法人 日本化学会の論文

著者

• Hashida Yoji

  Department of Chemistry, Faculty of Engineering, Gunma University

• Sekiguchi Shizen

  Department of Chemistry, Faculty of Engineering, Gunma University

• Matsui Kohji

  Department of Chemistry, Faculty of Engineering, Gunma University

• Tsunoda Shigeo

  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

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