Bifunctional compounds from reaction of alkoxy hydroperoxides with metal salts

Article abstract of DOI:10.1016/S0040-4020(01)91447-4

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 α,ω-disubstituted products in modest yields. By using ferric chloride, ω-chloro esters were obtained from the alkoxy hydroperoxides derived from olefinic esters.