Methyl-tri(nonyl)azanium;methyl(trioctyl)azanium;tris-decyl(methyl)azanium;trichloride

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

Procedure: The title compound was prepared essentially as in Example 3 using anhydrous potassium fluoride (12.8 g, 0.22 mol), anhydrous diethylene glycol dimethyl ether (diglyme, 106 g), methyltrialkyl(C8-C10)ammonium chloride (Adogen™ 464, available from Aldrich Chemical Company, 4 g), CF3COCF(CF3)2 (53.2 g, 0.20 mol, prepared essentially by the procedure of Smith et al., J. Am. Chem. Soc., 84, 4285 (1962)), and dimethyl sulfate (33.9 g, 0.72 mol). Aqueous potassium hydroxide was added to the reaction mixture (approximately 25 g of 50% solution), followed by water (200 mL). The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (b.p. 82-83° C.; yield of 45 g). The product identity was confirmed by GCMS and by FTIR. prepared essentially by the procedure of Smith et al., J The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (b.p. 82-83° C.; yield of 45 g)

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

Procedure: To a one liter round bottom flask equipped with an overhead stirrer, a condenser and an addition funnel was charged 12.8 g (0.22 mol) of anhydrous potassium fluoride, 106 g of anhydrous diglyme, 4 g of methyltrialkyl(C8-C10)ammonium chloride (ADOGEN™ 464, available from Aldrich Chemical Company), 53.2 g (0.20 mol) of CF3C(O)CF(CF3)2 (the perfluorinated ketone was prepared as described in Example 13), and 33.9 g (0.72 mol) of dimethyl sulfate. The resulting mixture was allowed to react at 40° C. for approximately 24 hours. Then approximately 25 g of a 50% aqueous potassium hydroxide solution was added to the reaction mixture, followed by 200 mL of water. The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (boiling point of 82-83° C.; yield of 45 g). The product identity, 2-methoxy-perfluoro(3-methylbutane), was confirmed by gcms and FTIR. To a one liter round bottom flask equipped with an overhead stirrer, a condenser and an addition funnel was prepared to react at 40° C. for approximately 24 hours The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (boiling point of 82-83° C.; yield of 45 g)

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

Procedure: To a one liter round bottom flask equipped with an overhead stirrer, a condenser and an addition funnel was charged 12.8 g (0.22 mol) of anhydrous potassium fluoride, 106 g of anhydrous diglyme, 4 g of methyltrialkyl(C8-C10)ammonium chloride (ADOGEN™ 464, available from Aldrich Chemical Company), 53.2 g (0.20 mol) of CF3C(O)CF(CF3)2 (the perfluorinated ketone was prepared as described in Example 13), and 33.9 g (0.72 mol) of dimethyl sulfate. The resulting mixture was allowed to react at 40° C. for approximately 24 hours. Then approximately 25 g of a 50% aqueous potassium hydroxide solution was added to the reaction mixture, followed by 200 mL of water. The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (boiling point of 82-83° C.; yield of 45 g). The product identity, 2-methoxy-perfluoro(3-methylbutane), was confirmed by gcms and FTIR. To a one liter round bottom flask equipped with an overhead stirrer, a condenser and an addition funnel was prepared to react at 40° C. for approximately 24 hours The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (boiling point of 82-83° C.; yield of 45 g)

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

Procedure: The title compound was prepared essentially as in Example 3 using anhydrous potassium fluoride (12.8 g, 0.22 mol), anhydrous diethylene glycol dimethyl ether (diglyme, 106 g), methyltrialkyl(C8-C10)ammonium chloride (Adogen™ 464, available from Aldrich Chemical Company, 4 g), CF3COCF(CF3)2 (53.2 g, 0.20 mol, prepared essentially by the procedure of Smith et al., J. Am. Chem. Soc., 84, 4285 (1962)), and dimethyl sulfate (33.9 g, 0.72 mol). Aqueous potassium hydroxide was added to the reaction mixture (approximately 25 g of 50% solution), followed by water (200 mL). The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (b.p. 82-83° C.; yield of 45 g) . The product identity was confirmed by GCMS and by FTIR. prepared essentially by the procedure of Smith et al., J The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (b.p. 82-83° C.; yield of 45 g)

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

Procedure: The title compound was prepared essentially as in Example 3 using anhydrous potassium fluoride (12.8 g, 0.22 mol), anhydrous diethylene glycol dimethyl ether (diglyme, 106 g), methyltrialkyl(C8-C10) ammonium chloride (Adogen™ 464, available from Aldrich Chemical Company, 4 g), CF3COCF(CF3)2 (53.2 g, 0.20 mol, prepared essentially by the procedure of Smith et al., J. Am. Chem. Soc., 84, 4285 (1962)), and dimethyl sulfate (33.9 g, 0.72 mol). Aqueous potassium hydroxide was added to the reaction mixture (approximately 25 g of 50% solution), followed by water (200 mL). The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (b.p. 82-83° C.; yield of 45 g). The product identity was confirmed by GCMS and by FTIR. prepared essentially by the procedure of Smith et al., J The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (b.p. 82-83° C.; yield of 45 g)

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

Procedure: The title compound was prepared essentially as in Example 3 using anhydrous potassium fluoride (12.8 g, 0.22 mol), anhydrous diethylene glycol dimethyl ether (diglyme, 106 g), methyltrialkyl(C8 -C10)ammonium chloride (Adogen™ 464, available from Aldrich Chemical Company, 4 g), CF3COCF(CF3)2 (53.2 g, 0.20 mol, prepared essentially by the procedure of Smith et al., J. Am. Chem. Soc., 84, 4285 (1962)), and dimethyl sulfate (33.9 g, 0.72 mol). Aqueous potassium hydroxide was added to the reaction mixture (approximately 25 g of 50% solution), followed by water (200 mL). The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (b.p. 82-83° C.; yield of 45 g). The product identity was confirmed by GCMS and by FTIR. prepared essentially by the procedure of Smith et al., J The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (b.p. 82-83° C.; yield of 45 g)

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

Procedure: The title compound was prepared essentially as in Example 3 using anhydrous potassium fluoride (12.8 g, 0.22 mol), anhydrous diethylene glycol dimethyl ether (diglyme, 106 g), methyltrialkyl(C8-C10)ammonium chloride (Adogen™ 464, available from Aldrich Chemical Company, 4 g), CF3COCF(CF3)2 (53.2 g, 0.20 mol, prepared essentially by the procedure of Smith et al., J. Am. Chem. Soc., 84, 4285 (1962)), and dimethyl sulfate (33.9 g, 0.72 mol). Aqueous potassium hydroxide was added to the reaction mixture (approximately 25 g of 50% solution), followed by water (200 mL). The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (b.p. 82-83° C.; yield of 45 g). The product identity was confirmed by GCMS and by FTIR. prepared essentially by the procedure of Smith et al., J The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (b.p. 82-83° C.; yield of 45 g)

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

Procedure: The title compound was prepared essentially as in Example 3 using anhydrous potassium fluoride (12.8 g, 0.22 mol), anhydrous diethylene glycol dimethyl ether (diglyme, 106 g), methyltrialkyl (C8 -Cl0) ammonium chloride (Adogen™ 464, available from Aldrich Chemical Company, 4 g), CF3COCF(CF3)2 (53.2 g, 0.20 mol, prepared essentially by the procedure of Smith et al., J. Am. Chem. Soc., 84, 4285 (1962)), and dimethyl sulfate (33.9 g, 0.72 mol). Aqueous potassium hydroxide was added to the reaction mixture (approximately 25 g of 50% solution), followed by water (200 mL). The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (b.p. 82-83° C.; yield of 45 g). The product identity was confirmed by GCMS and by FTIR. prepared essentially by the procedure of Smith et al., J The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (b.p. 82-83° C.; yield of 45 g)

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

Procedure: The title compound was prepared essentially as in Example 3 using anhydrous potassium fluoride (12.8 g, 0.22 mol), anhydrous diethylene glycol dimethyl ether (diglyme, 106 g), methyltrialkyl(C8-C10 )ammonium chloride (Adogen™ 464, available from Aldrich Chemical Company, 4 g), CF3COCF(CF3)2 (53.2 g, 0.20 mol, prepared essentially by the procedure of Smith et al., J. Am. Chem. Soc., 84, 4285 (1962)), and dimethyl sulfate (33.9 g, 0.72 mol). Aqueous potassium hydroxide was added to the reaction mixture (approximately 25 g of 50% solution), followed by water (200 mL). The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (b.p. 82-83° C.; yield of 45 g). The product identity was confirmed by GCMS and by FTIR. prepared essentially by the procedure of Smith et al., J The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (b.p. 82-83° C.; yield of 45 g)

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

Procedure: The title compound was prepared essentially as in Example 3 using anhydrous potassium fluoride (12.8 g, 0.22 mol), anhydrous diethylene glycol dimethyl ether (diglyme, 106 g), methyltrialkyl(C8-C10) ammonium chloride (Adogen™ 464, available from Aldrich Chemical Company, 4 g), CF3COCF(CF3)2 (53.2 g, 0.20 mol, prepared essentially by the procedure of Smith et al., J. Am. Chem. Soc., 84, 4285 (1962)), and dimethyl sulfate (33.9 g, 0.72 mol). Aqueous potassium hydroxide was added to the reaction mixture (approximately 25 g of 50% solution), followed by water (200 mL). The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (b.p. 82-83° C.; yield of 45 g). The product identity was confirmed by GCMS and by FTIR. prepared essentially by the procedure of Smith et al., J The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (b.p. 82-83° C.; yield of 45 g)

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

Procedure: The title compound was prepared essentially as in Example 3 using anhydrous potassium fluoride (12.8 g, 0.22 mol), anhydrous diethylene glycol dimethyl ether (diglyme, 106 g), methyltrialkyl(C8 -C10)ammonium chloride (Adogen™ 464, available from Aldrich Chemical Company, 4 g), CF3COCF(CF3)2 (53.2 g, 0.20 mol, prepared essentially by the procedure of Smith et al., J. Am. Chem. Soc., 84, 4285 (1962)), and dimethyl sulfate (33.9 g, 0.72 mol). Aqueous potassium hydroxide was added to the reaction mixture (approximately 25 g of 50% solution), followed by water (200 mL). The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (b.p. 82-83° C.; yield of 45 g). The product identity was confirmed by GCMS and by FTIR. prepared essentially by the procedure of Smith et al., J The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (b.p. 82-83° C.; yield of 45 g)

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

Procedure: The title compound was prepared essentially as in Example 3 using anhydrous potassium fluoride (12.8 g, 0.22 mol), anhydrous diethylene glycol dimethyl ether (diglyme, 106 g), methyltrialkyl(C8-C10)ammonium chloride (Adogen™ 464, available from Aldrich Chemical Company, 4 g), CF3COCF(CF3)2 (53.2 g, 0.20 mol, prepared essentially by the procedure of Smith et al., J. Am. Chem. Soc., 84, 4285 (1962)), and dimethyl sulfate (33.9 g, 0.72 mol). Aqueous potassium hydroxide was added to the reaction mixture (approximately 25 g of 50% solution), followed by water (200 mL). The resulting crude product was azeotropically distilled from the reaction mixture. The lower phase of the resulting distillate was separated from the upper phase, was washed with water, was dried over anhydrous sodium sulfate, and was distilled (b.p. 82-83° C.; yield of 45 g). The product identity was confirmed by GCMS and by FTIR. prepared essentially by the procedure of Smith et al., J The resulting crude product was azeotropically distilled from the reaction mixture The lower phase of the resulting distillate was separated from the upper phase was washed with water was dried over anhydrous sodium sulfate was distilled (b.p. 82-83° C.; yield of 45 g)