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

T E AndersonK A Woerpel
Published in: Organic letters (2020)
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.
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