Attack of a π center by F2 proceeds via electrophilic pathway forming the very short life α-fluorocarbocation. This, in turn, results in novel chemistry such as unprecedented nucleophilic attack of an angular terpenoid methyl on the α-fluorocarbocation resulting in a strained cyclopropane ring. On the other hand, F2 can react with H2O/CH3CN to form the relatively stable complex HOF/CH3CN possessing an electrophilic oxygen atom. Such atom is very reactive and can introduce oxygen into compounds which cannot be oxygenated by any other way.

F2 in organic synthesis: Formation of the unique α-fluorocarbocation and introduction of oxygen atom in “impossible” sites

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