Hydrolytic, reductive and pyrolytic decomposition of selected ozonolysis products. Water as an ozonization medium

Hydrolytic, reductive and pyrolytic decompositions of ozonolysis products formed in water were surveyed as potential preparative routes to aldehydes. Water is an effective ozonolysis medium and reacts with the transient zwitterion formed during ozonolysis in the same manner as participating solvents. Reductive decomposition proved to be superior to either hydrolytic or pyrolytic decomposition for the preparation of aldehydes. Pyrolytic decomposition, as carried out in the injection port of a gas chromatograph, gave varying amounts and types of products depending upon the type of ozonolysis product used. Interconversion of the various types of ozonolysis products, including ozonides, methoxy hydroperoxides, acetoxy hydroperoxides and hydroxy hydroperoxides, does not occur except under acid catalysis.