Oxidation of olefins with singlet oxygen

In terms of selectivity among several allylic positions in a molecule, the order of reactivity is CH2 CH3 CH in the case of trisubstituted alkenes, but becomes CH CH2 CH3 for disubstituted compounds. The proposed mechanism suggests that when the allylic intermediate is unsymmetrical, a mixture of reaction products will be found. Such a mixture has been observed in many instances. With terminal olefins, products resulting from double-bond migration are often found. [Pg.392]

Phenylselenyl bromide is an alternative reagent for allylic oxidation of alkenes. Addition takes place, and reaction of the adduct with acetic acid, followed by oxidation, generates the allylic acetate. [Pg.392]

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