Lemieux-Johnson oxidation

The Lemieux-Johnson oxidation is a chemical reaction named after its discoverers, R. U. Lemieux and W. S. Johnson, who published it in 1956. [cite journal
author = Pappo, R.; Allen, D. S., Jr.; Lemieux, R. U.; Johnson, W. S.
title = Osmium Tetroxide-Catalyzed Periodate Oxidation of Olefinic Bonds.
jpurnal = J. Org. Chem.
year = 1956
volume = 21
issue = 4
pages = 478–479
doi = 10.1021/jo01110a606] It involves the oxidation of an olefin to produce a 1,2-diol or 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.

References

ee also

*Upjohn dihydroxylation
*Sharpless asymmetric dihydroxylation