Criegee oxidation

[1] The rate of the reaction is highly dependent on the relative geometric position of the two hydroxyl groups, so much so that diols that are cis on certain rings can be reacted selectively as opposed to those that are trans on them.

[2] It was heavily stressed by Criegee that the reaction must be run in anhydrous solvents, as any water present would hydrolyze the lead tetraacetate; however, subsequent publications have reported that if the rate of oxidation is faster than the rate of hydrolysis, the cleavage can be run in wet solvents or even aqueous solutions.

[3] For example, glucose, glycerol, mannitol, and xylose can all undergo a Criegee oxidation in aqueous solutions, but sucrose cannot.

Because the substrates can be produced with specific stereochemistry, such as by Sharpless epoxidation of allylic alcohols, this process can yield chiral molecules.

[13] Criegee oxidations are commonly used in carbohydrate chemistry to cleave 1,2-glycols and differentiate between different kinds of glycol groups.