Alkenes, cleavage of, with

Fig. 17.26. Oxidative cleavages of alkenes with symmetrically (top) and asymmetrically (bottom) substituted C=C double bonds.

Henry, J. R., Weinreb, S. M. A convenient, mild method for oxidative cleavage of alkenes with Jones reagent/osmium tetraoxide. J. Org. Chem. 1993, 58, 4745. 

Recently it has been reported that oxidative cleavage of alkenes with catalytic osmium tetroxide is possible in the absence of water using the co-oxidant Oxone (KHSOs). In this case the diol is not formed and the intermediate osmate ester is oxidized by the Oxone and fragments to regenerate osmium tetroxide and release the carbonyl products. For example, the alkene 1-nonene gave octanoic acid (90% yield) under these conditions. 

Henry, J.R., and S.M. Weinreb, A Convenient, Mild Method for Oxidative Cleavage of Alkenes with Jones Reagent/OsmiumTetraoxide. J. Org. Chem. 58 4745 (1993). 

The following examples illustrate the results of potassium permanganate cleavage of alkenes with different substitution patterns. In the case where the product is a carboxylate salt, an addification step is required to obtain the carboxylic acid. 

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