Lemieux–Johnson oxidation

The classical Lemieux–Johnson oxidation often generates many side products, resulting in low reaction yields; however the addition of non-nucleophilic bases, such as 2,6-lutidine, can improve on this. OsO₄ may be replaced with a number of other Osmium compounds. Periodate may also be replaced with other oxidising agents, such as oxone.

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. This mixture became known as Lemieux reagent and has been used to determine the position of double bonds and for preparing carbonyl compounds. 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.