4,4,5,5-tetrachloro-2,2-difluoro-1,3-dioxolane

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

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 360 mL "Hastelloy" C shaker tube was charged with 113 g (0.5 mole) of tetrachloroethylene carbonate, sealed under nitrogen, cooled in a dry ice acetone mixture, evacuated, flushed with nitrogen, reevacuated and charged with 18 g (0.9 mole) of hydrogen fluoride and 194 g (1.8 mole) of sulfur tetrafluoride. The tube was agitated for 10 hours at 200° C. The tube was next chilled in an ice-water bath and then slowly vented to remove the excess SF4 and HF. The product was dumped from the tube into wet ice and allowed to stand a day. The organic phase was separated from the aqueous phase in a polyethylene separatory funnel, then stirred with a 30% aqueous solution of potassium carbonate to neutralize free acid. The product was dried over potassium carbonate and distilled at a reduced pressure. It boils at 126° C. at atmospheric pressure. The best yield of 4,4,5,5-tetrachloro-2,2,-difluoro-1,3-dioxolane was 73%. Infrared and nuclear magnetic resonance (NMR) spectra support the chemical structure (4) of this dioxolane. sealed under nitrogen evacuated flushed with nitrogen The tube was next chilled in an ice-water bath to remove the excess SF4 and HF to stand a day The organic phase was separated from the aqueous phase in a polyethylene separatory funnel stirred with a 30% aqueous solution of potassium carbonate The product was dried over potassium carbonate distilled at a reduced pressure

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 360 mL "Hastelloy" C shaker tube was charged with 113 g (0.5 mole) of tetrachloroethylene carbonate, sealed under nitrogen, cooled in a dry ice acetone mixture, evacuated, flushed with nitrogen, reevacuated and charged with 18 g (0.9 mole) of hydrogen fluoride and 194 g (1.8 mole) of sulfur tetrafluoride. The tube was agitated for 10 hours at 200° C. The tube was next chilled in an ice-water bath and then slowly vented to remove the excess SF4 and HF. The product was dumped from the tube into wet ice and allowed to stand a day. The organic phase was separated from the aqueous phase in a polyethylene separatory funnel, then stirred with a 30% aqueous solution of potassium carbonate to neutralize free acid. The product was dried over potassium carbonate and distilled at a reduced pressure. It boils at 126° C. at atmospheric pressure. The best yield of 4,4,5,5-tetrachloro-2,2,-difluoro-1,3-dioxolane was 73%. Infrared and nuclear magnetic resonance (NMR) spectra support the chemical structure (4) of this dioxolane. sealed under nitrogen evacuated flushed with nitrogen The tube was next chilled in an ice-water bath to remove the excess SF4 and HF to stand a day The organic phase was separated from the aqueous phase in a polyethylene separatory funnel stirred with a 30% aqueous solution of potassium carbonate The product was dried over potassium carbonate distilled at a reduced pressure

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

Procedure: A 300 mL, 3-neck glass flask equipped with magnetic stirrer, thermometer, Vigreux column with a water condenser to receiver, trap to a nitrogen tee and bubbler was charged with 1-propanol, 175 mL; zinc dust, 59.3 g; zinc chloride, 2.0 g. After heating to reflux, the 2,2-difluoro-4,4,5,5-tetrachloro-1,3-dioxolane (4j), 74.3 g, was added by syringe pump at 0.33 mL/minute. The addition was complete in 148 minutes. Distillation was begun 40 minutes after the start of the addition and continued for 6 hours until 72 mL of distillate was collected. The product was 98.7% pure desired dioxole, (3j), at 100% conversion of the dioxolane; the distillate which contained some propanol was redistilled through a 0.51 m spinning band column to separate the dioxole, (3j), b.p. 64°-65° C., at a purity of 98.6%. A 3.66 m×0.0064 m diameter 30% "Krytox" perfluoroether (Du Pont Co.) column at 60° C. was used in the analysis. The infrared spectrum was consistent with the structure. A 300 mL, 3-neck glass flask equipped with magnetic stirrer After heating to reflux The addition Distillation was begun 40 minutes after the start of the addition continued for 6 hours until 72 mL of distillate was collected was redistilled through a 0.51 m to separate the dioxole, (3j), b.p. 64°-65° C. at 60° C.

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 360 mL "Hastelloy" C. shaker tube was charged with 113 g (0.5 mole) of tetrachloroethylene carbonate, sealed under nitrogen, cooled in a dry ice acetone mixture, evacuated, flushed with nitrogen, reevacuated and charged with 18 g (0.9 mole) of hydrogen fluoride and 194 g (1.8 mole) of sulfur tetrafluoride. The tube was agitated for 10 hours at 200° C. The tube was next chilled in an ice-water bath and then slowly vented to remove the excess SF4 and HF. The product was dumped from the tube into wet ice and allowed to stand a day. The organic phase was separated from the aqueous phase in a polyethylene separatory funnel, then stirred with a 30% aqueous solution of potassium carbonate to neutralize free acid. The product was dried over potassium carbonate and distilled at a reduced pressure. It boils at 126° C. at atmospheric pressure. The best yield of 4,4,5,5-tetrachloro-2,2,-difluoro-1,3-dioxolane was 73%. Infrared and nuclear magnetic resonance (NMR) spectra support the chemical structure (4) of this dioxolane. sealed under nitrogen evacuated flushed with nitrogen The tube was next chilled in an ice-water bath to remove the excess SF4 and HF to stand a day The organic phase was separated from the aqueous phase in a polyethylene separatory funnel stirred with a 30% aqueous solution of potassium carbonate The product was dried over potassium carbonate distilled at a reduced pressure

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 360 mL "Hastelloy" C shaker tube was charged with 113 g (0.5 mole) of tetrachloroethylene carbonate, sealed under nitrogen, cooled in a dry ice acetone mixture, evacuated, flushed with nitrogen, reevacuated and charged with 18 g (0.9 mole) of hydrogen fluoride and 194 g (1.8 mole) of sulfur tetrafluoride. The tube was agitated for 10 hours at 200° C. The tube was next chilled in an ice-water bath and then slowly vented to remove the excess SF4 and HF. The product was dumped from the tube into wet ice and allowed to stand a day. The organic phase was separated from the aqueous phase in a polyethylene separatory funnel, then stirred with a 30% aqueous solution of potassium carbonate to neutralize free acid. The product was dried over potassium carbonate and distilled at a reduced pressure. It boils at 126° C. at atmospheric pressure. The best yield of 4,4,5,5-tetrachloro-2,2,-difluoro-1,3-dioxolane was 73%. Infrared and nuclear magnetic resonance (NMR) spectra support the chemical structure (4) of this dioxolane. sealed under nitrogen evacuated flushed with nitrogen The tube was next chilled in an ice-water bath to remove the excess SF4 and HF to stand a day The organic phase was separated from the aqueous phase in a polyethylene separatory funnel stirred with a 30% aqueous solution of potassium carbonate The product was dried over potassium carbonate distilled at a reduced pressure

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

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 360 mL "Hastelloy" C shaker tube was charged with 113 g (0.5 mole) of tetrachloroethylene carbonate, sealed under nitrogen, cooled in a dry ice acetone mixture, evacuated, flushed with nitrogen, reevacuated and charged with 18 g (0.9 mole) of hydrogen fluoride and 194 g (1.8 mole) of sulfur tetrafluoride. The tube was agitated for 10 hours at 200° C. The tube was next chilled in an ice-water bath and then slowly vented to remove the excess SF4 and HF. The product was dumped from the tube into wet ice and allowed to stand a day. The organic phase was separated from the aqueous phase in a polyethylene separatory funnel, then stirred with a 30% aqueous solution of potassium carbonate to neutralize free acid. The product was dried over potassium carbonate and distilled at a reduced pressure. It boils at 126° C. at atmospheric pressure. The best yield of 4,4,5,5-tetrachloro-2,2,-difluoro-1,3-dioxolane was 73%. Infrared and nuclear magnetic resonance (NMR) spectra support the chemical structure (4) of this dioxolane. sealed under nitrogen evacuated flushed with nitrogen The tube was next chilled in an ice-water bath to remove the excess SF4 and HF to stand a day The organic phase was separated from the aqueous phase in a polyethylene separatory funnel stirred with a 30% aqueous solution of potassium carbonate The product was dried over potassium carbonate distilled at a reduced pressure

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 360 mL "Hastelloy" C shaker tube was charged with 113 g (0.5 mole) of tetrachloroethylene carbonate, sealed under nitrogen, cooled in a dry ice acetone mixture, evacuated, flushed with nitrogen, reevacuated and charged with 18 g (0.9 mole) of hydrogen fluoride and 194 g (1.8 mole) of sulfur tetrafluoride. The tube was agitated for 10 hours at 200° C. The tube was next chilled in an ice-water bath and then slowly vented to remove the excess SF4 and HF. The product was dumped from the tube into wet ice and allowed to stand a day. The organic phase was separated from the aqueous phase in a polyethylene separatory funnel, then stirred with a 30% aqueous solution of potassium carbonate to neutralize free acid. The product was dried over potassium carbonate and distilled at a reduced pressure. It boils at 126° C. at atmospheric pressure. The best yield of 4,4,5,5-tetrachloro-2,2,-difluoro-1,3-dioxolane was 73%. Infrared and nuclear magnetic resonance (NMR) spectra support the chemical structure (4) of this dioxolane. sealed under nitrogen evacuated flushed with nitrogen The tube was next chilled in an ice-water bath to remove the excess SF4 and HF to stand a day The organic phase was separated from the aqueous phase in a polyethylene separatory funnel stirred with a 30% aqueous solution of potassium carbonate The product was dried over potassium carbonate distilled at a reduced pressure

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 360 mL "Hastelloy" C. shaker tube was charged with 113 g (0.5 mole) of tetrachloroethylene carbonate, sealed under nitrogen, cooled in a dry ice acetone mixture, evacuated, flushed with nitrogen, reevacuated and charged with 18 g (0.9 mole) of hydrogen fluoride and 194 g (1.8 mole) of sulfur tetrafluoride. The tube was agitated for 10 hours at 200° C. The tube was next chilled in an ice-water bath and then slowly vented to remove the excess SF4 and HF. The product was dumped from the tube into wet ice and allowed to stand a day. The organic phase was separated from the aqueous phase in a polyethylene separatory funnel, then stirred with a 30% aqueous solution of potassium carbonate to neutralize free acid. The product was dried over potassium carbonate and distilled at a reduced pressure. It boils at 126° C. at atmospheric pressure. The best yield of 4,4,5,5-tetrachloro-2,2,-difluoro-1,3-dioxolane was 73%. Infrared and nuclear magnetic resonance (NMR) spectra support the chemical structure (4) of this dioxolane. sealed under nitrogen evacuated flushed with nitrogen The tube was next chilled in an ice-water bath to remove the excess SF4 and HF to stand a day The organic phase was separated from the aqueous phase in a polyethylene separatory funnel stirred with a 30% aqueous solution of potassium carbonate The product was dried over potassium carbonate distilled at a reduced pressure

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

Procedure: A 300 mL, 3-neck glass flask equipped with magnetic stirrer, thermometer, Vigreux column with a water condenser to receiver, trap to a nitrogen tee and bubbler was charged with 1-propanol, 175 mL; zinc dust, 59.3 g; zinc chloride, 2.0 g. After heating to reflux, the 2,2-difluoro-4,4,5,5-tetrachloro-1,3-dioxolane (4j), 74.3 g, was added by syringe pump at 0.33 mL/minute. The addition was complete in 148 minutes. Distillation was begun 40 minutes after the start of the addition and continued for 6 hours until 72 mL of distillate was collected. The product was 98.7% pure desired dioxole, (3j), at 100% conversion of the dioxolane; the distillate which contained some propanol was redistilled through a 0.51 m spinning band column to separate the dioxole, (3j), b.p. 64°-65° C., at a purity of 98.6%. A 3.66 m×0.0064 m diameter 30% "Krytox" perfluoroether (Du Pont Co.) column at 60° C. was used in the analysis. The infrared spectrum was consistent with the structure. A 300 mL, 3-neck glass flask equipped with magnetic stirrer After heating to reflux The addition Distillation was begun 40 minutes after the start of the addition continued for 6 hours until 72 mL of distillate was collected was redistilled through a 0.51 m to separate the dioxole, (3j), b.p. 64°-65° C. at 60° C.

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 360 mL "Hastelloy" C shaker tube was charged with 113 g (0.5 mole) of tetrachloroethylene carbonate, sealed under nitrogen, cooled in a dry ice acetone mixture, evacuated, flushed with nitrogen, reevacuated and charged with 18 g (0.9 mole) of hydrogen fluoride and 194 g (1.8 mole) of sulfur tetrafluoride. The tube was agitated for 10 hours at 200° C. The tube was next chilled in an ice-water bath and then slowly vented to remove the excess SF4 and HF. The product was dumped from the tube into wet ice and allowed to stand a day. The organic phase was separated from the aqueous phase in a polyethylene separatory funnel, then stirred with a 30% aqueous solution of potassium carbonate to neutralize free acid. The product was dried over potassium carbonate and distilled at a reduced pressure. It boils at 126° C. at atmospheric pressure. The best yield of 4,4,5,5-tetrachloro-2,2,-difluoro-1,3-dioxolane was 73%. Infrared and nuclear magnetic resonance (NMR) spectra support the chemical structure (4) of this dioxolane. sealed under nitrogen evacuated flushed with nitrogen The tube was next chilled in an ice-water bath to remove the excess SF4 and HF to stand a day The organic phase was separated from the aqueous phase in a polyethylene separatory funnel stirred with a 30% aqueous solution of potassium carbonate The product was dried over potassium carbonate distilled at a reduced pressure