Lemieux-Johnson oxidation

From Wikipedia, the free encyclopedia

The Lemieux-Johnson oxidation is a chemical reaction named after its discoverers, R. U. Lemieux and W. S. Johnson, who published it in 1956.[1] It involves the oxidation of an olefin to produce a 1,2-diol or a two aldehydes. It is a two-step reaction, the first step consisting of the dihydroxylation of the carbon-carbon double bond by the Lemieux-Johnson reagent (sodium periodate-osmium tetroxide) and the second being the cleavage of the carbon-carbon single bond. The Lemieux-Johnson reaction ceases at the aldehydic stage of oxidation and therefore produces the same results as ozonolysis and subsequent reductive cleavage.

[edit] References

  1. ^ Pappo, R.; Allen, D. S., Jr.; Lemieux, R. U.; Johnson, W. S. "Osmium Tetroxide-Catalyzed Periodate Oxidation of Olefinic Bonds." J. Org. Chem. 1956, 21, 478.