Published July 15, 1981
| Version v1
Journal article
Reaction of tert-butoxy radicals with phenols. Comparison with the reactions of carbonyl triplets
Description
Tert-butoxy radicals generated in the photodecomposition of di-tert-butyl peroxide react efficiently with phenols to yield the corresponding phenoxy radicals. Typical rate constants in benzene at 220C are 3.3 x 108 and 1.6 x 109 M-1 s-1 for phenol and p-methoxyphenol, respectively. The process is considerably slower in polar solvents; e.g., when pyridine is used as cosolvent, the rate constant for phenol drops to 4.1 x 106 M-1 s-1 as a result of strong hydrogen bonding which decreases the reactivity of the phenolic O-H group. Isotope effects (H/D) are typically in the 3 to 5 range. 5 figures, 4 tables
Additional details
Publishing Information
- Journal Title
- J. Am. Chem. Soc.
- Journal Volume
- 103
- Journal Issue
- 14
- Series
- J. Am. Chem. Soc.
- Journal Page Range
- 4162-4166
- ISSN
- 0002-7863
INIS
- Country of Publication
- United States
- Country of Input or Organization
- United States
- INIS RN
- 12637387
- Subject category
- S37: INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY;
- Resource subtype / Literary indicator
- Numerical Data
- Descriptors DEI
- BUTOXY RADICALS; CHEMICAL REACTION KINETICS; CHEMICAL REACTIONS; DEUTERIUM; EXPERIMENTAL DATA; ISOTOPE EFFECTS; ORGANIC SOLVENTS; PHENOLS; TEMPERATURE DEPENDENCE
- Descriptors DEC
- ALKOXY RADICALS; AROMATICS; DATA; HYDROGEN ISOTOPES; HYDROXY COMPOUNDS; INFORMATION; ISOTOPES; KINETICS; LIGHT NUCLEI; NONAQUEOUS SOLVENTS; NUCLEI; NUMERICAL DATA; ODD-ODD NUCLEI; ORGANIC COMPOUNDS; RADICALS; REACTION KINETICS; SOLVENTS; STABLE ISOTOPES