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Archive for the ‘Criegee rearrangement’ Category

Named reaction refresher

Posted by naturalproductman on January 19, 2012

The Criegee rearrangement converts a tertiary alcohol into an alcohol and a ketone by using a peroxy acid and in turn forming peroxide intermediate that breaks down and forms the products.  In an ozonolysis, after the [3+2] between an ozone molecule and an alkene, the five membered ring breaks down to  a carbonyl and a carbonyl dioxide intermediate, which is called a “Criegee inermediate”.

Craig Taatjes and co-workers from Sandia National Laboratories have reported in Science on the observation of the Criegee intermediate by mass spec in the gas phase by reacting a methyl iodide radical and oxygen.


Science paper

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