Lemieux–Johnson oxidation
The Lemieux–Johnson or Malaprade–Lemieux–Johnson oxidation is a
The classical Lemieux–Johnson oxidation often generates many side products, resulting in low reaction yields; however the addition of non-nucleophilic bases, such as
History
The development of the Lemieux–Johnson oxidation was preceded by an analogous process, developed by Lemieux and Ernst Von Rudloff (sometimes called the Lemieux-Von Rudloff reaction), which used an aqueous solution of sodium periodate with a low (catalytic) concentration of potassium permanganate.[7] This mixture became known as Lemieux reagent[8][9] and has been used to determine the position of double bonds and for preparing carbonyl compounds.[10] Unlike the Lemieux–Johnson oxidation, which normally stops at the aldehyde, this older method could continue to give a mixture of aldehydes and carboxylic acids.[1]
See also
References
- ^ .
- ^ Hassner, Alfred; Stumer, C. (2002). "Malaprade–Lemieux–Johnson". Organic Syntheses Based on Name Reactions. Elsevier. p. 227.
- PMID 15355016.
- .
- .
- PMID 11942807.
- doi:10.1139/v55-208.
- ISBN 0471264199.
- ISBN 0471936235.
- doi:10.1139/v55-209.