PENTAFLUOROBENZENESULFONYL CHLORIDE

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Aniline 9.3 (44.6 g, 268 mmol) and 2,6-lutidine (32.8 mL, 282 mmol) were dissolved in 800 mL of acetone (the aniline only partly dissolved). An addition funnel was charged with C6F5SO2Cl (41.8 mL, 282 mmol) and the sulfonyl chloride was added over 15 minutes. During the addition, the starting material dissolved and a new precipitate (2,6-lutidine hydrochloride) formed. After 30 minutes, the 2,6-lutidine hydrochloride was removed by filtration and the filtrate concentrated under reduced pressure. The brown oily solid so produced was triturated with CH2Cl2 and the solid collected. A second batch of product was obtained by repeating the concentration, trituration, and filtration. After drying under high vacuum, 95.5 g (90%) of sulfonamide 9.4 was obtained as a pale yellow solid. only partly dissolved) During the addition the starting material dissolved

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 25 g of pentafluorobenzenesulfonyl chloride was dissolved in 100 ml of methanol under ice cooling and thereto, 100 g of a 25% aqueous tetramethylammonium hydroxide solution was gradually added. The resulting solution was stirred at room temperature for 3 hours, then, a solution of tetramethylammonium pentafluorobenzene sulfonate was obtained. This solution was used for the salt exchange with sulfonium salt or iodonium salt. 2) Synthesis of Di(4-t-Amylphenyl)iodonium Pentafluorobenzene Sulfonate (D-4)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under room temperature, a solution of 468 g of pentafluorobenzenesulfonyl chloride in acetone was added dropwise to an aqueous solution containing 964 g of ammonium chloride, during which a pH was adjusted to 7 with an aqueous sodium hydroxide solution. The precipitated product was filtered, and recrystallized from toluene to obtain 156 g of pentafluorobenzenesulfonamide as white crystals. A structure was confirmed by 1H-NMR, 19F-NMR and IR. The precipitated product was filtered recrystallized from toluene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To an aqueous solution of ammonium chloride was added dropwise an acetone solution of pentafluorobenzenesulfonyl chloride at room temperature. During addition, pH was adjusted to 7 by an aqueous sodium hydroxide solution. Precipitated product was filtered and recrystallized from toluene to give pentafluorobenzenesulfonamide. The structure was confirmed by 1H-NMR, 19F-NMR and IR. During addition, pH Precipitated product was filtered recrystallized from toluene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To an aqueous solution of ammonium chloride was added dropwise an acetone solution of pentafluorobenzenesulfonyl chloride at room temperature. During addition, pH was adjusted to 7 by an aqueous sodium hydroxide solution. Precipitated product was filtered and recrystallized from toluene to give pentafluorobenzenesulfonamide. The structure was confirmed by 1H-NMR, 19F-NMR and IR. During addition, pH Precipitated product was filtered recrystallized from toluene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Aniline 9.3 (44.6 g, 268 mmol) and 2,6-lutidine (32.8 mL, 282 mmol) were dissolved in 800 mL of acetone (the aniline only partly dissolved). An addition funnel was charged with C6F5SO2Cl (41.8 mL, 282 mmol) and the sulfonyl chloride was added over 15 minutes. During the addition, the starting material dissolved and a new precipitate (2,6-lutidine hydrochloride) formed. After 30 minutes, the 2,6-lutidine hydrochloride was removed by filtration and the filtrate concentrated under reduced pressure. The brown oily solid so produced was triturated with CH2Cl2 and the solid collected. A second batch of product was obtained by repeating the concentration, trituration, and filtration. After drying under high vacuum, 95.5 g (90%) of sulfonamide 9.4 was obtained as a pale yellow solid. only partly dissolved) During the addition the starting material dissolved

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Aniline 9.3 (44.6 g, 268 mmol) and 2,6-lutidine (32.8 mL, 282 mmol) were dissolved in 800 mL of acetone (the aniline only partly dissolved). An addition funnel was charged with C6F5SO2Cl (41.8 mL, 282 mmol) and the sulfonyl chloride was added over 15 minutes. During the addition, the starting material dissolved and a new precipitate (2,6-lutidine hydrochloride) formed. After 30 minutes, the 2,6-lutidine hydrochloride was removed by filtration and the filtrate concentrated under reduced pressure. The brown oily solid so produced was triturated with CH2Cl2 and the solid collected. A second batch of product was obtained by repeating the concentration, trituration, and filtration. After drying under high vacuum, 95.5 g (90%) of sulfonamide 9.4 was obtained as a pale yellow solid. only partly dissolved) During the addition the starting material dissolved

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir: