Oxygen → HCID 20502259, compound

HRID 2198959Notes

Reaction equation

HRID 2198959 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:31]=O>>[F:30][C:2]1([F:1])[O:31][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

3

Reactant 2

HCID 977OxygenHCID 86738869HCID 86738869, compound

Product 1

HCID 20502259HCID 20502259, compoundYield 31%

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 distillation 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, 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. distillationThe distillation
  3. addition25 ml of CFCl2CF2Cl and some calcium sulfate were added
  4. customseparation
  5. dry with materialThe lower layer was dried over calcium sulfate

Sources & evidence

ORD record
ord-4a925d082640429a9b33ee5b5e430d97
Source dataset
uspto-grants-1982_11
Patent number
US04360645

Reaction notes

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