Fluoride Ion → HCID 9837031, compound

Participants

Reaction Steps

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.

Provenance & Evidence