Acyl fluorides
Class of chemical compounds
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Through Aryl group and Hydrolysis
Preparation
The several routes to acyl fluorides can be roughly subdivided into three approaches.
Halide exchange
Acyl chlorides react with hydrogen fluoride to give acyl fluorides. This reaction is relevant to the use of electrofluorination route to perfluorinated carboxylic acids, such as PFOA.
S- and P-based reagents
The OH group of carboxylic acids can be converted to fluoride using various oxophilic reagents. Aromatic (as well as aliphatic) acyl fluorides can be prepared from carboxylic acids with PPh3 and fluoride sources. Cyanuric fluoride as well as sulfur tetrafluoride also convert carboxylic acids to acyl fluorides.
- SF4 + RCO2H → SOF2 + RC(O)F + HF
Fluorophosgene
Salts of trifluoromethoxide react with carboxylic acids to give acyl fluorides. The process entails formation of difluorophosgene. Solutions of trifluoromethoxide are prepared by displacement from aryl trifluoromethyl ethers.
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Reactions
A common reaction of acyl fluorides is hydrolysis to the carboxylic acid.
Perfluoroacyl fluorides react with fluoride salts to perfluoroalkoxides:
- C3F7COF + F− → C4F9O−
Utility
Acyl fluorides are intermediates in the electrochemical fluorination (ECF) route to perfluorocarboxylic acids, such as perfluorooctanoic acid).