1-Dodecanethiol → 1-Pentafluoroethylthiododecane

Participants

Reaction Steps

2.0 ml of methylene chloride, 0.10 ml (0.42 mmol) of 1-dodecanethiol and 87 mg (0.42 mmol) of 2,6-di-tert-butyl-4-methylpyridine were added to a flask, and 198 mg (0.42 mmol) of pentafluoroethylphenyliodonium trifluoromethanesulfonate was added thereto in small portions while stirring at room temperature, followed by stirring at room temperature for 20 minutes. The resulting white precipitate was filtered and subjected to column chromatography of silica gel. Iodobenzene and the product was eluted with pentane and purified by gas chromatography to obtain 1-pentafluoroethylthiododecane as an oily substance. Yield, 87%.

Provenance & Evidence