Strain-Promoted Oxidation of Methylenecyclopropane Derivatives using N‑Hydroxyphthalimide and Molecular Oxygen in the Dark

The hydroperoxidation of alkylidenecyclopropanes and other strained alkenes using an N-hydroxylamine and molecular oxygen occurred in the absence of catalyst, initiator, or light. The oxidation reaction proceeds through a radical pathway that is initiated by autoxidation of the alkene substrate. The hydroperoxides were converted to their corresponding alcohols and ketones under mild conditions.