Abstract
Reaction of /sup 3/CH/sub 2/, produced by reaction of arc-generated carbon atoms with CF/sub 3/, with oxygen in the presence of alkenes oxygenates alkenes 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 initio calculations demonstrate that the difluorodioxirane is more stable than the corresponding carbonyl oxide and that closure of the carbonyl oxide to the dioxirane should be rapid. The results of these calculations are compared to those on the parent CH/sub 2/O/sub 2/ system. Reaction of carbon atoms with oxygen and alkenes in the absence of CF/sub 3/ gives nonstereospecific epoxidation presumably through the intermediacy of O atoms.
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