Oxidative cleavage of olefins by ozone

Better yields are often obtained when ozone is used for oxidative cleavage of olefins to carboxylic acids or of cycloalkenes to dicarboxylic acids. Olefinic double bonds are very much more easily attacked by ozone than are aromatic systems, so that arylethylene derivatives can be successfully treated with ozone without appreciable effect on the ring. If the ozonide which is formed initially is decomposed with water, the aldehyde is obtained together with hydrogen peroxide and other products  

To convert olefins into carboxylic acids in this way it is preferable to oxidize the primary fission products of the ozonide in a subsidiary reaction. Particularly good results were obtained by Asinger using a hot suspension of silver oxide116 and by Wilms using peracetic acid 117 Wilms thus obtained adipic acid in yields of about 90% from cyclohexene  

Aldehydes can be obtained homogeneously from ozonides by reductive cleavage, which can be effected either by zinc in glacial acetic acid or by catalytic hydrogenation of the ozonide118,119 in the presence of a 1 19 palladium-calcium carbonate catalyst.120 Adipdialdehyde has thus been obtained from cyclohexene in 60-70% yield 121 

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