1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Ethenyl-perfluoro-3-oxapentanesulfonyl fluoride
Reaction equation
I[CH2:2][CH2:3][C:4]([C:7]([O:10][C:11]([C:14]([S:17]([F:20])(=[O:19])=[O:18])([F:16])[F:15])([F:13])[F:12])([F:9])[F:8])([F:6])[F:5].C1CCN2C(=NCCC2)CC1>>[CH2:2]=[CH:3][C:4]([C:7]([O:10][C:11]([C:14]([S:17]([F:20])(=[O:19])=[O:18])([F:15])[F:16])([F:12])[F:13])([F:9])[F:8])([F:6])[F:5]Participants
Procedure
The crude reaction solution from above containing ICH2CH2CF2CF2OCF2CF2SO2F was treated with an excess of DBU at room temperature for 4 hours. 19F NMR analysis showed no effect on the —SO2F group, and the triplet of CF2CH2— was changed into doublet×triplet at 121 ppm (Jd=7.8 Hz, Jt=3.6 Hz), indicating the desired reaction occurred to yield CH2═CHCF2CF2OCF2CF2SO2F. Addition of water to dissolve DBU/HI solid, and the bottom perfluorinated N-methyl morpholine solution was isolated. From F-NMR, no more I—CF2CF2OCF2CF2SO2F was observed in the isolated solution. The solution was dried over MgSO4. After filtration and rotary evaporation to remove the solvent, 22 g product was obtained (89% isolated yield; bp=115-116° C.). 19F NMR showed the chemical shifts at +43 ppm (—SO2F), −83.8 ppm (m, —CF2O—), −89.2 ppm (txt, —CF2O—), −114 ppm (dxt, —CF2SO2F) and 120 ppm (dxt, —CF2CH═). Also, H1 NMR confirmed the formation of CH2═CH— with chemical shift at 5.7˜6.3 ppm (m).
Workup
- customThe crude reaction solution from
- customreaction
Sources & evidence
- ORD record
- ord-995c6b2e83e245379db2a824bcfb7e5b
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187416B2
Reaction notes
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