Ketene → Fluoride Ion

HRID 1657954Notes

Reaction equation

HRID 1657954 reaction equation
[F:1][C:2]([CH:5]([C:9](F)=[O:10])[C:6]([F:8])=[O:7])([F:4])[F:3].C=C=O>>[F-:1].[F:1][C:2]([C:5]([C:6]([F:8])=[O:7])=[C:9]=[O:10])([F:4])[F:3]

Participants

4

Reactant 2

HCID 10038KeteneHCID 12951306Trifluoromethylmalonyl fluoride

Product 2

HCID 28179Fluoride IonYield 40%HCID 23236247TrifluoromethylfluorocarbonylketeneYield 15%

Procedure

A mixture of 17.6 g (0.10 mol) of trifluoromethylmalonyl fluoride (containing ca. 5% of the ketene) and 24 g (0.3 mol) of SO3 was heated and crude distillate was redistilled to provide 11.9 g (40%) of pyrosulfuryl fluoride, bp 51°-54°C, and 2.4 g (15%) of trifluoromethylfluorocarbonylketene, bp 58°-59.5°C. Pyrosulfuryl fluoride was identified by comparison of bp, infrared spectrum and nmr spectrum with those reported for authentic samples. The ketene was shown in infrared to be the same as that prepared in Example 4.

Workup

  1. temperaturewas heated
  2. distillationcrude distillate was redistilled

Sources & evidence

ORD record
ord-ea9a72fbba5c4254828a98c211957850
Source dataset
uspto-grants-1976_06
Patent number
US03962325

Reaction notes

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