1,1,1,4,4,4-hexafluorobut-2-yne

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.7 g (41 nmol) of gaseous hexafluoro-2-butyne were passed at below (-50)° C. into a suspension, cooled to (-70)° C., of 9 g (36 mmol) of α-bromo-4-chlorobenzaldehyde methylhydrazone in 100 ml of toluene. The mixture was subsequently heated to (-25)° C., and 8.4 g (83 mmol) of triethylamine were added dropwise at this temperature. After the mixture had been stirred for 2 hours at this temperature and for a further 16 hours at approx. 20° C., it as washed with water, dried over magnesium sulfate and finally concentrated. into a suspension, cooled to (-70)° C The mixture was subsequently heated to (-25)° C it as washed with water dried over magnesium sulfate finally concentrated

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.7 g (41 nmol) of gaseous hexafluoro-2-butyne were passed at below (-50)° C. into a suspension, cooled to (-70)° C., of 9 g (36 mmol) of α-bromo-4-chlorobenzaldehyde methylhydrazone in 100 ml of toluene. The mixture was subsequently heated to (-25)° C., and 8.4 g (83 mmol) of triethylamine were added dropwise at this temperature. After the mixture had been stirred for 2 hours at this temperature and for a further 16 hours at approx. 20° C., it as washed with water, dried over magnesium sulfate and finally concentrated. into a suspension, cooled to (-70)° C The mixture was subsequently heated to (-25)° C it as washed with water dried over magnesium sulfate finally concentrated

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

Procedure: Hexafluoro-2-butyne (21.0 g, 0.13 mol) was transferred into a reaction bottle and 2-methylfuran (12.86 g, 0.157 mol) was added. This resulting mixture bottle was sealed and heated for 15 hr. at 120° C. After cooling, the excess 2-methylfuran was rotoevaporated in vacuo at rt, to give crude title product (29 g, 92%), which was used directly. was added This resulting mixture bottle was sealed heated for 15 hr at 120° C After cooling was rotoevaporated in vacuo at rt

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

Procedure: Hexafluoro-2-butyne is slowly bubbled through a 55°-60° C. solution of p-chloroacetophenone oxime (17.0 g, 0.10 mol), methanol (80 mL) and potassium tert-butoxide (1.12 g, 0.01 mol) over a 5 hour period. The solvent is removed in vacuo to obtain a liquid which is poured into water and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give an oil. The oil is chromatographed using silica gel and eluted with 1% ethylacetate in methylene chloride to 5% ethyl acetate in methylene chloride to give p-chloro-0-[1,2-bis(trifluoromethyl)vinyl]acetophenone oxime, vinyl-(Z) as a yellow liquid (21.5 g, 65%) and 2-(p-chlorophenyl)-4,5-trans-bis(trifluoromethyl)-1-pyrrolin-5-ol as a white solid (2.35 g, mp 152.5°-153° C., 7%). The solvent is removed in vacuo to obtain a liquid which extracted with ether The combined organic extracts are washed sequentially with water and brine dried over anhydrous sodium sulfate concentrated in vacuo to give an oil The oil is chromatographed eluted with 1% ethylacetate in methylene chloride to 5% ethyl acetate in methylene chloride

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

Procedure: Hexafluoro-2-butyne is slowly bubbled through a 55°-60° C. solution of p-chloroacetophenone oxime (17.0 g, 0.10 mol), methanol (80 mL) and potassium tert-butoxide (1.12 g, 0.01 mol) over a 5 hour period. The solvent is removed in vacuo to obtain a liquid which is poured into water and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give an oil. The oil is chromatographed using silica gel and eluted with ethylacetate in methylene chloride to 5% ethyl acetate in methylene chloride to give p-chloro-0-[1,2-bis(trifluoromethyl)vinyl]acetophenone oxime, vinyl-(Z) as a yellow liquid (21.5 g, 65%) and 2-(p-chlorophenyl)-4,5-trans-bis(trifluoromethyl)-1-pyrrolin-5-ol as a white solid (2.35 g, mp 152.5°-153° C., 7%). The solvent is removed in vacuo to obtain a liquid which extracted with ether The combined organic extracts are washed sequentially with water and brine dried over anhydrous sodium sulfate concentrated in vacuo to give an oil The oil is chromatographed eluted with ethylacetate in methylene chloride to 5% ethyl acetate in methylene chloride

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

Procedure: Reaction of cyclopentadiene with hexafluorobut-2-yne at 100° C. for 24 hours gives 2,3-bis(trifluoromethyl)bicyclo [2.2.1] heptadiene which, upon hydrogenation over platinum, gives 2,3-bis(trifluoromethyl)bicyclo [2.2.1] heptane.

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

Procedure: Reaction of cyclopentadiene with hexafluorobut-2-yne at 100° C. for 24 hours gives 2,3-bis(trifluoromethyl)bicyclo [2.2.1] heptadiene which, upon hydrogenation over platinum, gives 2,3-bis(trifluoromethyl)bicyclo [2.2.1] heptane.

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

Procedure: Reaction of cyclopentadiene with hexafluoro-but-2-yne at 100° C for 24 hours gives 2,3-bis (trifluoromethyl) bicyclo [2.2.1] heptadiene which, upon hydrogenation over platinum, gives 2,3-bis(trifluoromethyl) bicyclo [2.2.1] heptane.

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hexafluoro-2-butyne (21.0 g, 0.13 mol) was transferred into a reaction bottle and treated with 2-methylfuran (12.86 g, 0.157 mol). This resulting mixture bottle was sealed and heated for 15 hours at 120° C. After cooling, the excess 2-methylfuran was rotoevaporated in vacuo at room temperature, to give the crude title product (29 g, 92%), which was used directly. This resulting mixture bottle was sealed After cooling was rotoevaporated in vacuo at room temperature

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

Procedure: Hexafluoro-2-butyne is slowly bubbled through a 55°-60° C. solution of p-chloroacetophenone oxime (17.0 g, 0.10 mol), methanol (80 mL) and potassium tert-butoxide (1.12 g, 0.01 mol) over a 5 hour period. The solvent is removed in vacuo to obtain a liquid which is poured into water and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give an oil. The oil is chromatographed using silica gel and eluted with 1% ethylacetate in methylene chloride to 5% ethyl acetate in methylene chloride to give p-chloro-0-[1,2-bis(trifluoromethyl)vinyl]acetophenone oxime, vinyl-(Z) as a yellow liquid (21.5 g, 65%) and 2-(p-chlorophenyl)-4,5-trans-bis(trifluoromethyl)-1-pyrrolin-5-ol as a white solid (2.35 g, mp 152.5°-153° C., 7%). The solvent is removed in vacuo to obtain a liquid which extracted with ether The combined organic extracts are washed sequentially with water and brine dried over anhydrous sodium sulfate concentrated in vacuo to give an oil The oil is chromatographed eluted with 1% ethylacetate in methylene chloride to 5% ethyl acetate in methylene chloride

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.7 g (41 nmol) of gaseous hexafluoro-2-butyne were passed at below (-50)° C. into a suspension, cooled to (-70)° C., of 9 g (36 mmol) of α-bromo-4-chlorobenzaldehyde methylhydrazone in 100 ml of toluene. The mixture was subsequently heated to (-25)° C., and 8.4 g (83 mmol) of triethylamine were added dropwise at this temperature. After the mixture had been stirred for 2 hours at this temperature and for a further 16 hours at approx. 20° C., it as washed with water, dried over magnesium sulfate and finally concentrated. into a suspension, cooled to (-70)° C The mixture was subsequently heated to (-25)° C it as washed with water dried over magnesium sulfate finally concentrated

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

Procedure: Hexafluoro-2-butyne (21.0 g, 0.13 mol) was transferred into a reaction bottle and 2-methylfuran (12.86 g, 0.157 mol) was added. This resulting mixture bottle was sealed and heated for 15 hr. at 120° C. After cooling, the excess 2-methylfuran was rotoevaporated in vacuo at rt, to give crude title product (29 g, 92%), which was used directly. was added This resulting mixture bottle was sealed heated for 15 hr at 120° C After cooling was rotoevaporated in vacuo at rt