Strain-Promoted Oxidation of Methylenecyclopropane Derivatives using <i>N</i>-Hydroxyphthalimide and Molecular Oxygen in the Dark
Thomas E. Anderson, K. A. Woerpel
Abstract
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.
Topics & Concepts
ChemistryAutoxidationHydroxylamineMethylenecyclopropaneMolecular oxygenPhotochemistryAlkeneCatalysisOxygenSubstrate (aquarium)Strain (injury)Organic chemistryMedicinal chemistryMedicineGeologyOceanographyInternal medicineOxidative Organic Chemistry ReactionsRadical Photochemical ReactionsCatalytic C–H Functionalization Methods