The reactivity of CF3OF has been widely studied especially in halogenated olefinic systems [1] and its use in pharmaceutical synthesis as a mild radical and electrophilic fluorinating agent is also well documented.
On the other hand, the chemical behavior of the perfluoro-methyl-hypofluorite with aromatic substrates is much less studied. Up to now few and scattered data regarding its use as electrophilic fluorinating agent of variously substituted aromatic compounds are found in the literature.
The reactivity of CF3OF with simple electron rich and electron poor aromatics (α,α,α-trifluoro-toluene, toluene, benzene, chloro-benzene, methoxybenzene) has been investigated. The possibility of selectively bind the trifluoro-methoxy group by varying the reaction conditions has been explored.
The perfluoro-hypofluorite was obtained via direct fluorination of carbon monoxide. This reaction is recognized as a gas phase, radical and thus fast exothermic reaction. In the absence of proper temperature control the reaction is also prone to thermal run-away.
To obtain a clean stream of CF3OF the direct fluorination of carbon monoxide has been studied and optimized in a newly designed stainless steel microreactor [2]. Its performances, in terms of operability and selectivity, have been compared with a standard reactor assembly.
This research resulted in the development of a one-step synthesis of aromatic-trifluoro-ethers via radical addition [3]
