Lemieux-Johnson oxidation
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. It involves the oxidation of an olefin to produce a 1,2-diol or two aldehyde
s. 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.
Chemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...
named after its discoverers, R. U. Lemieux and W. S. Johnson, who published it in 1956. It involves the oxidation of an olefin to produce a 1,2-diol or two aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
s. 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
Sodium periodate
Sodium periodate is the sodium salt of periodic acid. It can refer to two different chemical compounds, sodium metaperiodate , which has the formula NaIO4, and sodium orthoperiodate , which has the formula Na2H3IO6...
-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
Ozonolysis
Ozonolysis is the cleavage of an alkene or alkyne with ozone to form organic compounds in which the multiple carbon–carbon bond has been replaced by a double bond to oxygen...
and subsequent reductive cleavage.
See also
- Upjohn dihydroxylationUpjohn dihydroxylationUpjohn dihydroxylation is an organic reaction converting an alkene to a cis vicinal diol, and was developed by V. VanRheenen, R. C. Kelly and D. Y. Cha of the Upjohn Company, USA in 1976...
- Sharpless asymmetric dihydroxylationSharpless asymmetric dihydroxylationSharpless asymmetric dihydroxylation is the chemical reaction of an alkene with osmium tetroxide in the presence of a chiral quinine ligand to form a vicinal diol....
- Raymond Lemieux