Tris(benzimidazo)-1,3,5-triazine from the Thermolysis of 2-Aryloxybenzimidazoles
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概要
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2-Aryloxybenzimidazoles gave tris(benzimidazo)-[1,2-<I>a</I>: 1′,2′-<I>c</I>: 1″,2″-<I>e</I>]-1,3,5-triazine and phenol in almost quantitative yields upon heating at 230–250 °C, while in the reaction in cumene small amounts of 2-aryloxy-1,2′-dibenzimidazole and dicumyl were obtained along with the major products. On the other hand, 2-phenylthiobenzimidazole gave diphenyl disulfide and 1,2′-dibenzimidazole, together with tris(benzimidazo)-1,3,5-triazine. The thermolysis is assumed to proceed by step-by-step radical processes involving the formation of such intermediates as 2-aryloxy-1,2′-dibenzimidazole and 2-aryloxy-1,2′-1′,2″-trisbenzimidazole.
- 公益社団法人 日本化学会の論文
著者
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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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Fukushima Yoshiaki
Department of Chemistry, Gunma University
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Ishida Sadahiro
Department of Chemistry, 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