Hydrolysis carbonyl difluoride

Sodium nitrite in dimethylformamide acts as a nucleophile and reacts with perfluoropropene to generate a perfluoroalkyl nitrite anion The intermediate carbanion undergoes intramolecular nitrosation with loss of carbonyl difluoride to give tnfluoroacetic acid upon hydrolysis [5] (equation 6)... 

Before handling carbonyl difluoride, personnel should be equipped with suitable leak detection equipment and HF Antidote Gel (see Section 13.1.5). A solution of concentrated aqueous ammonia enables the detection of leaks by forming copious white fumes on contact of the respective vapours. Larger leaks are apparent from the formation of white fumes resulting from the hydrolysis of the COFj in moist air, and from the detection of the irritating and pungent odour. Any areas of equipment exposed to a COFj leakage should be cleaned up to remove any acid formed. 

The high boiling point of trifluoro(phenyl)-/l4-sulfane (4) enables reactions to be performed at atmospheric pressure in normal glassware. It is important that all reactions are carried out under anhydrous conditions and contact with glass be kept to a maximum of several hours to avoid hydrolysis (caution hydrolysis will liberate hydrogen fluoride). It has been reported that trifluoro(phenyl)-24-sulfane can convert carbonyl compounds to gem-difluorides, e.g. 5-6. 

The bicyclic fused iodoxole oxide 531, the aliphatic analog of IBX, has been prepared by the fluorination of a tricoordinate 1,2-iodoxetane 234 (Section 2.1.8.9) with xenon difluoride followed by hydrolysis of the intermediate, non-isolable, difluoride 530 (Scheme 2.149) [701]. Compound 531 has a similar reactivity to that of IBX and can oxidize alcohols and sulfides to the corresponding carbonyl compounds and sulfoxides, respectively, in good yields under mild conditions. 

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