Dicarboxylic Acids from Ozonolysis of Cycloalkenes

Article abstract of DOI:10.1021/jo00189a026

The "superior" method for the synthesis of dicarboxylic acids by ozonolysis of cycloalkenes with 1 molar equiv of ozone in an ether-type solvent, followed by hydrogenation over Lindlar's catalyst, has been found not to yield dicarboxylic acids directly, as claimed in the Soviet literature, unless excess ozone is employed.The peroxidic ozonolysis products obtained by us have been characterized and are quite different from those reported by the Russians.Thus, their mechanisms do not appear to be applicable.Ozonolysis of cycloalkenes in an acetic acid-formic acid mixture, followed by further oxidation with molecular oxygen, is a much better method for the dicarboxylic acid syntheses.