Reaction of Chlorophenols with Nickl Peroxide

Sugita, Jitsuo

doi:10.1246/nikkashi1948.87.7_741

Cited by 5 publications

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“…Ketals 6 and 7 , however, were easily hydrolyzed to their respective substituted quinones ( 8 and 9 ) in acid solution (eq 2); both quinones were isolated and characterized: 8 , MS, 1 H and 13 C NMR, IR, HRMS, and elemental analysis; 9 , MS, 1 H and 13 C NMR, IR, HRMS, elemental analysis and X-ray crystallography. Compound 8 has been reported previously as a product in the oxidation of 2 with various metal oxides and nickel peroxide . Our melting point (116.5−118 °C) differed somewhat from the reported melting points 134.5−136 °C 2 and 120−124 °C .…”

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“…Compound 8 has been reported previously as a product in the oxidation of 2 with various metal oxides and nickel peroxide . Our melting point (116.5−118 °C) differed somewhat from the reported melting points 134.5−136 °C 2 and 120−124 °C . We repeated the oxidation of 2 with PbO 2 as reported 2 and obtained 8 as established by its mass spectra (GC-MS); however, the product from 2 and PbO 2 always contained an unknown impurity that we were unable to remove even with column chromatography.…”

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Formation of Dimer-Type Ketals in the Reaction of 2,4,6-Trichlorophenol and 2,4,6-Trichloro-m-cresol with Calcium Hypochlorite in Methanol: Conversion to Quinones and Other Compounds

et al. 2002

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2,4,6-Trichlorophenol (2) and 2,4,6-trichloro-m-cresol (5) react with calcium hypochlorite (Ca(OCl)(2)) in MeOH to give respectively dimer-type ketals 2-(2',4',6'-trichlorophenoxy)-4,4-dimethoxy-6-chlorocyclohexadien-2,5-one (6) and 2-(3'-methyl-2',4',6'-trichlorophenoxy)-4,4-dimethoxy-5-methyl-6-chlorocyclohexadien-2,5-one (7). Ketal 6, which was too unstable to be isolated, and 7 hydrolyzed in H(2)O/HCl to 2-(2',4',6'-trichlorophenoxy)-6-chloro-1,4-benzoquinone (8) and 2-(3'-methyl-2',4',6'-trichlorophenoxy)-5-methyl-6-chloro-1,4-benzoquinone (9), respectively. Ketal 6 and quinone 8 were also produced when 2 and Ca(OCl)(2) reacted in DMF, followed by addition of MeOH and H(2)O, respectively. The mechanisms of these reactions are examined. Conversion of the ketals and quinones to other products is described.

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Formation of Dimer-Type Ketals in the Reaction of 2,4,6-Trichlorophenol and 2,4,6-Trichloro-m-cresol with Calcium Hypochlorite in Methanol: Conversion to Quinones and Other Compounds

et al. 2002

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The oxidative coupling of 2,6‐disubstituted phenols with PbO₂ and other metal oxides

Dort¹,

Jonge²,

Mijs³

1968

J. polym. sci., C Polym. symp.

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The main product in the oxidative coupling of 2,6‐dimethyl phenol with PbO2 and other metal oxides is poly‐2,6‐dimethyl phenylene oxide (Mn up to 20,000). The influence of the temperature, the solvent, and the addition of small amounts of various substances on the course of the reactions is discussed. The addition of an amine to the reaction mixture suppresses the diphenoquinone formation, and polymers with much higher molecular weights may be obtained. Infrared and NMR endgroup analyses show that the polymers prepared with PbO2 and in the absence of amines are branched. On the addition of increasing amounts of amines to the reaction mixtures the degree of branching gradually decreases. Mechanisms for the branching reaction are suggested. The effect of soluble onium salts, such as trimethylcetylammonium bromide, on the course of the oxidative coupling is mentioned (slow reactions giving polymers with high molecular weights). Aromatic polyethers are also obtained in the metal oxide oxidations of 2,6‐disubstituted phenols with bulky substituents, such as: 2,6‐diethyl phenol, 2,6‐diisopropyl phenol, and 2,6‐dimethoxy phenol. Some properties of the polymers are given. There are indications that the reactions go by way of metal phenolates.

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Oxidation of Organic Compounds with Nickel Peroxide

George

1986

Organic Syntheses by Oxidation With Metal Compounds

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Reaction of Chlorophenols with Nickl Peroxide

Cited by 5 publications

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Formation of Dimer-Type Ketals in the Reaction of 2,4,6-Trichlorophenol and 2,4,6-Trichloro-m-cresol with Calcium Hypochlorite in Methanol: Conversion to Quinones and Other Compounds

Formation of Dimer-Type Ketals in the Reaction of 2,4,6-Trichlorophenol and 2,4,6-Trichloro-m-cresol with Calcium Hypochlorite in Methanol: Conversion to Quinones and Other Compounds

The oxidative coupling of 2,6‐disubstituted phenols with PbO₂ and other metal oxides

Oxidation of Organic Compounds with Nickel Peroxide

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Reaction of Chlorophenols with Nickl Peroxide

Cited by 5 publications

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Formation of Dimer-Type Ketals in the Reaction of 2,4,6-Trichlorophenol and 2,4,6-Trichloro-m-cresol with Calcium Hypochlorite in Methanol: Conversion to Quinones and Other Compounds

Formation of Dimer-Type Ketals in the Reaction of 2,4,6-Trichlorophenol and 2,4,6-Trichloro-m-cresol with Calcium Hypochlorite in Methanol: Conversion to Quinones and Other Compounds

The oxidative coupling of 2,6‐disubstituted phenols with PbO2 and other metal oxides

Oxidation of Organic Compounds with Nickel Peroxide

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The oxidative coupling of 2,6‐disubstituted phenols with PbO₂ and other metal oxides