Fluorides, acyl fluorinating agents

The perchloryl fluoride [7616-94-6] FCIO, the acyl fluoride of perchloric acid, is a stable compound. Normally a gas having a melting poiat of —147.7° C and a boiling poiat of —46.7°C, it can be prepared by electrolysis of a saturated solution of sodium perchlorate ia anhydrous hydrofluoric acid. Some of its uses are as an effective fluorinating agent, as an oxidant ia rocket fuels, and as a gaseous dielectric for transformers (69). 

There are two types of hypofluorite compounds that have been prepared, the perfluoroalkyl hypofluorites, such as CF3OF, and the acyl hypofluorites, such as CH3C02F. The fluorines of such compounds are very deshielded and thus have significantly positive chemical shifts (Scheme 7.15). Also shown is the powerful electrophilic fluorinating agent, perchloryl fluoride. 

Replacement of three fluorine atoms in cyanuric fluoride 55 was applied for construction biologically active molecules of deazapurine type [95]. Cyanuric fluoride mediated reaction of chiral Na-tritylamino acids leads to the corresponding acyl fluorides 155 which are powerful acylating agents for peptide synthesis... 

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