Nucleophilic Behavior of the Phenyl Radical in the Hydrogen Abstraction Reaction from Substituted Toluenes, A Contribution to the Study of the Phenyldiazenyl Radical

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.