Oxygen → HCID 20502259, compound

HRID 851339Notes

Reaction equation

HRID 851339 reaction equation
[F:1][C:2]([F:30])=[C:3]([F:29])[C:4]([F:28])([F:27])[O:5][C:6]([F:26])([F:25])[C:7]([F:24])([F:23])[C:8]([F:22])([F:21])[O:9][C:10]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([F:19])[C:11]=1[F:20].O=O.S([O-])([O-])(=O)=[O:34].[Ca+2]>C(C(Cl)(F)F)(Cl)(Cl)F>[F:30][C:2]1([F:1])[O:34][C:3]1([F:29])[C:4]([F:27])([F:28])[O:5][C:6]([F:26])([F:25])[C:7]([F:23])([F:24])[C:8]([F:21])([F:22])[O:9][C:10]1[C:11]([F:20])=[C:12]([F:19])[C:13]([F:18])=[C:14]([F:17])[C:15]=1[F:16]

Participants

5

Reactant 3

HCID 977OxygenHCID 24497Calcium SulfateHCID 86738869HCID 86738869, compound

Product 1

HCID 20502259HCID 20502259, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6428Cfc 113Solvent

Procedure

A 100-ml metal tube lined with stainless steel and charged with 105.3 g (0.22 mol) of perfluoro(7-phenoxy-4-oxa-1-heptene) was heated at 140° while oxygen was pressured in intermittently until no pressure drop was observed. The liquid product mixture was fractionated to afford 78.5 g of distillate, bp 37°-70° (3 min). The distillate was shaken with 1 liter of ice water, and then 25 ml of CFCl2CF2Cl and some calcium sulfate were added to hasten separation. The lower layer was dried over calcium sulfate and fractionated to give 33.3 g (31%) of perfluoro(7-phenoxy-1,2-epoxy-4-oxaheptane), bp 55° (1.9 mm). IR (CCl4): 6.47 (epoxide ring), 6.58 (aromatic C=C), 8-9μ (CF, C-O). NMR (CCl4): 19F -84.1 (m, 2F, OCF2), -84.6 (m, 2F, OCF2), -129.0 (s, 2F, CF2), -151.8 (m, 2F, arom. CF), -155.1 (t, JFF 21.0 Hz, 1F, arom. CF), -156.6 (t, JFF 17.9 Hz, 1F, ring CF), and -161.7 ppm (m, 2F, arom. CF), with AB groupings at -7382, -7534, -7566, and -7719 Hz (m, 2F) for CF2 adjacent to epoxide ring and at -10381 and -10424 Hz (d of t, JFF 18.8, 9.8 Hz, 1F) and --10600 and -10642 Hz (d, JFF 17.3 Hz, 1F) for epoxide CF2.

Workup

  1. customto afford 78.5 g of distillate, bp 37°-70° (3 min)
  2. customseparation
  3. dry with materialThe lower layer was dried over calcium sulfate

Sources & evidence

ORD record
ord-0d5b6414ea8e4c8c96ffdb6947ae2ea8
Source dataset
uspto-grants-1983_05
Patent number
US04384128

Reaction notes

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