Hexafluoropropylene → 1,2-Oxathietane, 3,4,4-trifluoro-3-(trifluoromethyl)-, 2,2-dioxide

HRID 1702849

Reaction equation

HRID 1702849 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([F:7])=[C:4]([F:6])[F:5].[S:10](=[O:13])(=[O:12])=[O:11]>>[F:1][C:2]([F:9])([F:8])[C:3]1([F:7])[C:4]([F:6])([F:5])[O:13][S:10]1(=[O:12])=[O:11]

Participants

3

Reactant 2

HCID 8302HexafluoropropyleneHCID 24682Sulfur trioxide

Product 1

HCID 27762401,2-Oxathietane, 3,4,4-trifluoro-3-(trifluoromethyl)-, 2,2-dioxide

Procedure

A mixture of commercial liquid sulfur trioxide (10 ml) and hexafluoropropene (45 g, 0.30 mol) was sealed in a Carius tube at liquid nitrogen temperature, mixed well at 25° C., allowed to stand for 4 days at 25° C., and finally heated in a steam bath for 6 hours. From two such tubes, there was obtained by distillation, 3-(trifluoromethyl)-3,4,4-trifluoro-1-oxa-2-thiacyclobutane 2,2-dioxide (2-hydroxy-1-trifluoromethyl-1,2,2-trifluoroethane sulfonic acid sultone, D. C. England, M. A. Dietrich and R. V. Lindsey, Jr., J. Amer. Chem. Soc., 82, 6181 (1960)) (25 g, 22%) bp 44° C., and pentafluoro-2-propenyl fluorosulfate (hereinafter referred to as perfluoroallyl fluorosulfate) (73 g, 63%), bp 58°-60° C.

Workup

  1. customwas sealed in a Carius tube at liquid nitrogen temperature
  2. additionmixed well at 25° C.
  3. temperaturefinally heated in a steam bath for 6 hours

Sources & evidence

ORD record
ord-5e2d8884d96b4b4eb643f6693d6ebd04
Source dataset
uspto-grants-1982_09
Patent number
US04349650

Linked notes

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