5-IODOOCTAFLUORO-3-OXAPENTANESULFONYL FLUORIDE

反応条件: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the teachings of Beckerbauer et al, op.cit., U.S. Pat. No. 5,958,822, (CH3O)3SiCH2CH2CF2CF2OCF2CF2SO2F was prepared as follows. To a stirred mixture of 85 g (0.2 mol) of ICF2CF2OCF2CF2SO2F available from the Shanghai Institute of Organic Chemistry, Shanghai, China, and 32 g (0.215 mol) of (CH3O)3SiCH═CH2 (Aldrich Chemical Company) was added 0.5 g of benzoyl peroxide (Aldrich) at 90 to 95° C. in N2 and the resulting mixture was stirred at 95° C. for 40 minutes. An additional 0.5 g of benzoyl peroxide was added and the mixture was stirred for 4 hours more and then evacuated to remove excess starting materials. After the mixture was cooled to room temperature, 59 g of (C4H9)3SnH was slowly added and the mixture was stirred at room temperature overnight and distilled to give 60.9 g of liquid (CH3O)3SiCH2CH2CF2CF2OCF2CF2SO2F having a purity of greater than 99% and boiling point of 55° C./3 mm Hg. 19F NMR(CDCl3): +44.9 (s, 1F), −82.6 (m, 2F), −87.4 (m, 2F), −112.6 (s, 2F), −120.7 (t, J=15 Hz, 2F), 1HNMR: 3.60 (s, 9H), 2.10 (m, 2H), 0.70 (m, 2H). the mixture was stirred for 4 hours more evacuated to remove excess starting materials After the mixture was cooled to room temperature 59 g of (C4H9)3SnH was slowly added the mixture was stirred at room temperature overnight distilled

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 12.56 grams (0.03 mol) of 5-iodooctafluoro-3-oxapentanesulfonyl fluoride (Synquest) was taken in a flask in water and excess amount of KOH (0.06 mol, 3.31 grams) was added and the resulting mixture was heated under stirring at 80° C. for six hours. To this reaction mixture (after cooling to room temperature) was added 1:2 v/v THF/water solution of triphenyl sulfonium bromide (0.03 mol, 10.14 grams) dropwise over a period of one hour with stirring. After the addition, the reaction mixture was further stirred for additional 3 hours at room temperature. Upon completion, the target compound triphenylsulfonium 5-iodooctafluoro-3-oxapentafluoro sulfonate was extracted using methylene chloride. It was washed at least three times with DI water. Methylene chloride was evaporated to get a pale yellow liquid. It was redissolved in methylene chloride and precipitated into hexanes. Yield was 82%. Melting point (capillary) 110-112° C. the resulting mixture was heated To this reaction mixture (after cooling to room temperature) with stirring After the addition the reaction mixture was further stirred for additional 3 hours at room temperature Upon completion, the target compound triphenylsulfonium 5-iodooctafluoro-3-oxapentafluoro sulfonate was extracted It was washed at least three times with DI water Methylene chloride was evaporated to get a pale yellow liquid precipitated into hexanes Melting point (capillary) 110-112° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 7.82 g (100 mmol) of benzene, 8.52 g (20 mmol) of 5-iodooctafluoro-3-oxapentanesulfonyl fluoride, 4.84 g (20 mmol) of benzoyl peroxide, 0.36 g (2 mmol) of copper (II) acetate, and 100 mL of acetic acid were refluxed for 4 hrs at 115° C. Then the mixture was stirred at room temperature overnight. The mixture was diluted with water (˜100 mL), and the product was extracted with hexane and washed with water until neutral pH was obtained. The solvent was removed to yield dark yellow oil. The product was purified by distillation under reduced pressure (˜27 inch Hg). The first faction was composed of a mixture of the product plus iodobenzene (2.8 g, approximately 1:1 ratio). The second fraction consisted of 2.1 g of pure product (colorless oil) (28% yield). the product was extracted with hexane washed with water until neutral pH was obtained The solvent was removed to yield dark yellow oil The product was purified by distillation under reduced pressure (˜27 inch Hg) The first faction was composed of a mixture of the product plus iodobenzene (2.8 g, approximately 1:1 ratio)

反応条件: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the teachings of Beckerbauer et al, op.cit., U.S. Pat. No. 5,958,822, (CH3O)3SiCH2CH2CF2CF2OCF2CF2SO2F was prepared as follows. To a stirred mixture of 85 g (0.2 mol) of ICF2CF2OCF2CF2SO2F available from the Shanghai Institute of Organic Chemistry, Shanghai, China, and 32 g (0.215 mol) of (CH3O)3SiCH═CH2 (Aldrich Chemical Company) was added 0.5 g of benzoyl peroxide (Aldrich) at 90 to 95° C. in N2 and the resulting mixture was stirred at 95° C. for 40 minutes. An additional 0.5 g of benzoyl peroxide was added and the mixture was stirred for 4 hours more and then evacuated to remove excess starting materials. After the mixture was cooled to room temperature, 59 g of (C4H9)3SnH was slowly added and the mixture was stirred at room temperature overnight and distilled to give 60.9 g of liquid (CH3O)3SiCH2CH2CF2CF2OCF2CF2SO2F having a purity of greater than 99% and boiling point of 55° C./3 mm Hg. 19F NMR(CDCl3): +44.9 (s, 1F), −82.6 (m, 2F), −87.4 (m, 2F), −112.6 (s, 2F), −120.7 (t, J=15 Hz, 2F), 1HNMR: 3.60 (s, 9H), 2.10 (m, 2H), 0.70 (m, 2H). the mixture was stirred for 4 hours more evacuated to remove excess starting materials After the mixture was cooled to room temperature 59 g of (C4H9)3SnH was slowly added the mixture was stirred at room temperature overnight distilled