Oxidations hypofluorous acid-acetonitrile complex

The hypofluorous acid/acetonitrile complex has also been used for the oxidation of secondary alcohols and for the Baeyer Villiger oxidation of ketones.24-25... 

It is possible that the iodine and base could be generated in the way cited earlier for the oxidation of 2-methylnaphtho-quinone. Fluorine forms a hypofluorous acid-acetonitrile complex when it is passed into wet acetonitrile. This complex has been used to convert olefins, such as undecylenic acid, oleic, and cinnamic acid to the corresponding epoxides in 90% yields.294 The disadvantages of the process are the need to handle the very reactive fluorine and the need to recycle the by-product hydrogen fluoride. 

Though it requires vigorous conditions and is less common than nucleophilic epoxidation, electrophilic epoxidation of aperfluoroalkene is possible with the potent combination of chromic oxide and fluorosulfonic acid, providing another route to hexafluoropropylene oxide (1). As a further example of electrophilic attack, hexa-fluoro Dewar benzene (3) is transformed into either a mono- or a diepoxide by the powerful hypofluorous acid-acetonitrile complex.The fact that the much weaker electrophile MCPBA readily epoxides such electron-deficient alkenes as ethyl pentafiuoromethacrylate (4) suggests that it actually reacts via nucleophilic attack at the [3-carbon. 

An easily prepared acetonitrile complex of hypofluorous acid (HOF-CH3CN) serves an excellent reagent for the oxidation of alkenes with pendant alcohol or carboxylic acid functionalities <1996TL531>. 

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