Bifunctional compounds from reaction of alkoxy hydroperoxides with metal salts

Alkoxy hydroperoxides, obtained by ozonizing olefins in alcoholic solution, were treated with ferrous sulfate. C-C bond scission and radical formation was followed by dimerization of the radicals formed. Ozonides reacted similarly. Acyclic and cyclic olefins, including a cyclic enol ether, gave rise to a range of ,ω-disubstituted products in modest yields. By using ferric chloride, ω-chloro esters were obtained from the alkoxy hydroperoxides derived from olefinic esters.