Sulfur tetrafluoride reaction with amides

The reaction of tertiary amides of p-toluenesulfinic acid with sulfur tetrafluoride proceeds with cleavage of the S-N bond to give aminosulfur trifluorides 8 and p-toluenesulfinyl fluoride in good yield. The products can be readily separated by distillation.213... 

The reaction of amides with sulfur tetrafluoride or with carbonyl difluoride leads to fluorinated compounds with a nitrogen substituent at the difluoromethylene or trifluoromcthyl group and thus these reactions are not covered here. 

Many aldehydes and ketones have been converted to g m-difluoro compounds with sulfur tetrafluoride (SF4), " including quinones, which give 1,1,4,4-tetra-fluorocyclohexadiene derivatives. With ketones, yields can be raised and the reaction temperature lowered, by the addition of anhydrous HF. Carboxylic acids, acyl chlorides, and amides react with SF4 to give 1,1,1-trifluorides. In these cases the first product is the acyl fluoride, which then undergoes the ge i-difluorination reaction ... 

The most general and useful application of sulfur tetrafluoride is replacement of carbonyl oxygen and hydroxy groups by fluorine. The reaction has broad scope and is effective with all carbonyl and hydroxy compounds. Alcohols are converted into monofluoro derivatives 1, aldehydes, ketones and quinones into gew-difluoro compounds 2 and 3, and carboxylic acids, acid anhydrides, acid halides and amides into trifluoromethyl compounds 4. 

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