Harries Ozonide Reaction (Ozonolysis)

C. Harries, Ann. 343, 311 (1905).

Treatment of olefins with ozone as a method of cleaving olefinic linkages. On hydrolysis or catalytic hydrogenation the initially formed ozonide yields two molecules of carbonyl compounds:

Reviews: P. S. Bailey, Chem. Rev. 58, 925 (1958); L. J. Chinn, Selection of Oxidants in Synthesis: Oxidation at the Carbon Atom (Dekker, New York, 1971) pp 151-160; P. S. Bailey, Ozonation in Organic Chemistry vols. 1 and 2 (Academic Press, New York, 1978, 1982). Mechanism: R. Criegee, Rec. Chem. Prog. 18, 111 (1957); R. W. Murray, Acc. Chem. Res. 1, 313 (1968); M. Miura et al., J. Org. Chem. 50, 1504 (1985). Applications: J. Z. Gillies et al., J. Am. Chem. Soc. 110, 7991 (1988); K. Griesbaum, V. Ball, Tetrahedron Lett. 35, 1163 (1994).