What is 'passive' oxidation?

What is the correct experimental protocol for carrying out Lemieux-Johnson-Jin 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.http://en.wikipedia.org/wiki/Lemieux%E2%80%93Johnson_oxidation#cite_note-1 It involves the oxidation of an http://en.wikipedia.org/wiki/Olefin to produce a 1,2-diol or two aldehyde/ketone/or boths. 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. In 2004 Prof. Zhendong Jin’s group published a seminal paper on the topic of Lemieux-Johnson oxidation in Org. Lett.http://en.wikipedia.org/wiki/Lemieux%E2%80%93Johnson_oxidation#cite_note-HuaZ-2 Jin and his coworkers discovered that the addition of 2,6-lutidine can effectively suppress the formation of α-hydroxy ketone side products as well as many other side products, accelerate the rate of the desired reaction, and dramatically improve the reaction yield.

• Answer:

  In the article we were discussing yesterday, there's a very promising method that combines both methods. I think it's worth trying. This method they suggest is very clever, I'd say. NaIO4 is used to regenerate KMnO4 after oxidation. It's a great advantage of this method that work-up is simple. Column chromatography is usually unwanted. It is time-consuming, large amounts of solvents are necessary, and there are losses, which, when working with miligrams of a substance is not to be underestimated. The procedure is described in detail on page 3 of the article, in the column on the right. I think it's pretty self-explanatory. You only need to re-calculate the amounts of substances according to your alkene.