Fluoride Ion → HCID 9837031, compound
Reaction equation
[F-].[C:2]1([N:12]([S:19]([F:22])([F:21])[F:20])[C:13]2C=CC=CC=2)[C:11]2[C:6](=CC=CC=2)[CH:5]=[CH:4][CH:3]=1>>[CH3:13][N:12]([S:19]([F:22])([F:20])[F:21])[C:2]1[CH:11]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
Deoxofluorination of cyclooctanol with diarylaminosulfur trifluorides proceeds rapidly at −78° C. in CH2Cl2 to produce cyclooctylfluoride and cyclooctene with the former predominating (Table 8). Differing ratios of fluoride to olefin were observed with the various aromatic substituted trifluorides. The sterically hindered N-naphthyl-N-phenylaminosulfur trifluoride reacted quite slowly affording only a 10% conversion of starting material to products after 16 h at room temperature. A rapid conversion to the monofluoride was obtained with N-methyl-N-phenylaminosulfur trifluoride. Among the alkoxyalkyl compounds 35-41 (Table 5), the phenyl substituted aminosulfur trifluoride (35) proved to be the most reactive affording fluorination at −78° C. in 1 h as compared to the methyl and bisalkoxyalkyl compounds (37, 41, respectively) which required longer reaction times (˜3 hr) at −78° C. to effect the same conversion.
Workup
- customaffording only a 10% conversion of starting material to products after 16 h at room temperature
Sources & evidence
- ORD record
- ord-705ac5a41558417a96cb0ea9d51248d7
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06242645B1
Reaction notes
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