Oxygen Donation by an Intermadiate in the Reaction of 3CF2 with O2

Article abstract of DOI:10.1021/ja00220a045

Reaction of ³CF2, produced by reaction of arc-generated carbon atoms with CF3, with oxygen in the presence of alkenes oxygenates to epoxides, which are formed stereospecifically, and carbonyl compounds.The reaction is postulated to involve the intermediacy of difluorodioxirane, which transfers oxygen stereospecifically to the alkene.Ab inito calculations demonstrate that the difluorodioxirane is more stable than the corresponding carbonyl oxide to the dioxirane should be rapid.The results of these calculations are compared to those on the parent CH2O2 system.Reaction of carbon atoms with oxigen and alkenes in the absence of CF3 gives nonstereospecific epoxidation presumably through the intermediacy of O atoms.