Sensitized Photooxygenation of Olefins

Abstract

Sensitized photooxygenations of olefins have been extensively studied; they represent convenient methods for the introduction of oxygen at specific sites. When an aerated solution containing a monolefin, diene, or polyene, and a sensitizer is irradiated with light that can be absorbed by the sensitizer, oxygenated products are formed whose nature depends upon the structure of the substrate and the lability of the initial photoproducts under the reaction conditions. The ready reducibility of hydroperoxides to alcohols enhances the synthetic usefulness of these photoxygenations In this chapter, coverage is restricted to molecules with one or more carbon-carbon double bonds. Keywords: sensitized photooxygenation; olefins; rearrangements; reduction; monoolefins; solvent effects; steric effects; electronic effects; dioxetane reaction; allylic hydroperoxides; 1,4-epidioxides; experimental conditions