Facile Autoxidation of 2-(4-Hydroxy- phenyl)-3,3-dimethylmethylenecyclopropane. The Radical Stabilizing Ability of the Phenoxide Group
摘要:
2-(4-Hydroxyphenyl)-3,3-dimethylmethylenecyclopropane undergoes rapid reaction with O-2 at room temperature to give a dioxolane, A chain mechanism involving ring opening of a phenoxy radical is proposed. Conversion of the title compound to the phenoxide results in a remarkably accelerated methylenecyclopropane rearrangement. Computational studies suggest that the intermediate biradical is greatly stabilized by the phenoxide substituent.
Facile Autoxidation of 2-(4-Hydroxy- phenyl)-3,3-dimethylmethylenecyclopropane. The Radical Stabilizing Ability of the Phenoxide Group
摘要:
2-(4-Hydroxyphenyl)-3,3-dimethylmethylenecyclopropane undergoes rapid reaction with O-2 at room temperature to give a dioxolane, A chain mechanism involving ring opening of a phenoxy radical is proposed. Conversion of the title compound to the phenoxide results in a remarkably accelerated methylenecyclopropane rearrangement. Computational studies suggest that the intermediate biradical is greatly stabilized by the phenoxide substituent.