Bulletin of the Chemical Society of Japan · 1977 · 20 citations · 13 references
Natural SciencesChemistryChemical KineticsMolecular PhysicsOrganic ChemistryChemical Reaction KineticsHalogen ChemistryKinetic Isotope EffectsOrganic SynthesisOxidation ReactionsRadical ReactionsDeuterium Isotope EffectHalogen Radical ChemistryHydrogen Abstraction ReactionsKinetic Isotope Effect AnalysisNucleophilic ReactivityRadical Reaction Kinetics
Abstract Phenyl radicals derived from benzoyl peroxide (BPO) showed nucleophilic behavior, rho=+0.18 (metaseries) for the hydrogen abstraction reaction from substituted toluenes at 80 °C, and a kinetic deuterium isotope effect, kH⁄kD=3.73±0.2, was found for toluene. Comparison of these results with those for the phenyl radicals from phenylazotriphenylmethane (PAT) leads to the suggestion that the phenyldiazenyl radicals derived from PAT abstract hydrogen from toluene to yield benzene, which should amount to about 50% of the total benzene formed.
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