Triethylamine → 1-Cyclooctene

Participants

Reaction Steps

Procedure for the fluorination of alcohols (examples 74-84): To a suspension of the disubstituted aminodifluorosulfinium salt (1.5 mmol), triethylamine trihydrofluoride (326 μL, 2.0 mmol) and triethylamine (139 μL, 1.0 mmol) in dichloromethane (3.0 mL), at room temperature and under nitrogen, is added cyclooctanol (132 μl, 1.0 mmol). The reaction mixture is stirred for 19 h, then quenched with a 5% aqueous sodium bicarbonate solution, stirred for 15 min, and the resulting mixture was extracted using dichloromethane. The organic phases were combined, dried over magnesium sulfate and filtered through a pad of silica gel. Solvents were evaporated to provide fluorocyclooctane of admixed with cyclooctene as a clear oil (refer to the following table for yields and product distribution).

Provenance & Evidence