Does the reaction of Cu sup + with H sub 2 O sub 2 give OH radicals A study of aromatic hydroxylation

Journal Article · Fri Dec 08 04:00:00 EST 1989 · Journal of Organic Chemistry; (USA)

DOI:https://doi.org/10.1021/jo00286a024· OSTI ID:6971360

Eberhardt, M K; Ramirez, G; Ayala, E ^[1]

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1. Univ. of Puerto Rico, San Juan (Puerto Rico)

The reaction of Cu{sup +} with H{sub 2}O{sub 2} was studied by using the isomer distribution obtained with fluorobenzene, anisole, and nitrobenzene as a probe for OH radicals. The reaction with benzene in presence of 5 {times} 10{sup {minus}2} M Cu{sup 2+} gave a maximum yield of 69% phenol. The isomer distributions obtained with fluorobenzene, anisole, and nitrobenzene are almost identical with those obtained in the radiation-induced hydroxylation under similar conditions. In experiments with benzene and nitrobenzene they have shown that Cu{sup 3+} produced via Cu{sup 2+} + OH does not hydroxylate these aromatic compounds in neutral or weakly acidic solutions (pH 5.0-6.0). They therefore conclude that in the reaction of Cu{sup +} with H{sub 2}O{sub 2} the OH radical is the major reactive species that reacts with aromatic compounds.

• OSTI ID: 6971360
• Journal Information: Journal of Organic Chemistry; (USA), Journal Name: Journal of Organic Chemistry; (USA) Vol. 54:25; ISSN JOCEA; ISSN 0022-3263
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400201* -- Chemical & Physicochemical Properties
400600 -- Radiation Chemistry
AROMATICS
BENZENE
CHARGED PARTICLES
CHEMICAL REACTIONS
COPPER IONS
DATA
DATA ANALYSIS
EXPERIMENTAL DATA
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN PEROXIDE
HYDROXYL RADICALS
HYDROXYLATION
INFORMATION
IONS
MEASURING INSTRUMENTS
MEASURING METHODS
NUMERICAL DATA
ORGANIC COMPOUNDS
OXYGEN COMPOUNDS
PEROXIDES
RADICALS