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bismuth
tris-(trifluoromethyl)methyl hypochlorite
A
Bi(3+)*3(CF3)3CO(1-) = Bi{(CF3)3CO}3
B
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
byproducts: (CF3)2CO, CF3Cl, Cl2; reaction mixt. maintained at 0°C for 40 h and at room temp. for 94 h and between 25 and 30°C for 6 h; addn. of additional (CF3)3COCl; volatiles removed at room temp. under vac.; elem. anal.; | A 93% B n/a |
(trifluoromethyl)trimethylsilane
Hexafluoroacetone
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With potassium fluoride In acetonitrile Mechanism; a) 9 h, -40 deg C, b) 3 h, 18 deg C; other carbonyl compounds, variation of conditions: xfluorinated tertiary alcohols and alkoxides from nucleophilic trifluoromethylation of carbonyl compounds; | 91.3% |
With potassium fluoride In acetonitrile 1) -40 deg C, 9 h, 2) 18 deg C, 3 h; | 91.3% |
(trifluoromethyl)trimethylsilane
trifluoroacetic anhydride
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With tetramethylammonium fluoride In 1,2-dimethoxyethane at -30 - 20℃; | 87% |
1,1,1-trichloro-3,3,3-trifluoro-2-(trifluoromethyl)propan-2-ol
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With antimony pentafluoride for 3h; Heating; | 85% |
With antimony pentafluoride |
Carbonyl fluoride
(trifluoromethyl)trimethylsilane
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With potassium fluoride In acetonitrile for 18h; -40 deg C to r.t.; | 77.1% |
nanofluoro-tert-butylamine
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With trifluoroacetic acid; sodium nitrite In water at 20℃; for 1h; | 70% |
Vinylidene fluoride
C4BrF9O
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
Hexafluoroacetone
Conditions | Yield |
---|---|
at -88 - 24℃; for 12h; Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; | A n/a B n/a C 31% D n/a |
at -88 - 24℃; for 12h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; |
C4BrF9O
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
Hexafluoroacetone
Conditions | Yield |
---|---|
at -88 - 24℃; for 12h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; |
trifluorormethanesulfonic acid
B
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
bis(nonafluoro-tert-butoxy)(pentafluorophenylsulfanyl)trifluorophenylsulfur(IV)
water
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
bis(pentafluorophenyl) disulfide
C
pentafluorophenyl pentafluorobenzenethiosulfonate
Conditions | Yield |
---|---|
hydrolysis at 25°C; |
bis(nonafluoro-tert-butoxy)(trifluoromethyl)trifluoromethylsulfanylsulfur(IV)
water
A
Bis(trifluoromethyl)disulfid
B
Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester
C
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
hydrolysis at 25°C; |
nanofluoro-tert-butylamine
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
1,1,1,3,3,3-hexafluoro-2-nitroso-2-trifluoromethyl-propane
Conditions | Yield |
---|---|
With sodium nitrite In sulfuric acid At 0°C then at -10°C; | |
With NaNO2 In sulfuric acid aq. H2SO4; At 0°C then at -10°C; |
nonafluoro-tert-butyl trifluoromethanesulfinate
A
Carbonyl fluoride
B
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
C
silicon tetrafluoride
Conditions | Yield |
---|---|
byproducts: SO2; hydrolyzes in moist air at 25°C; |
CrO2{(CF3)3CO}2
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
chromic acid
Conditions | Yield |
---|---|
With water detected by NMR; |
C16H12F9NO4
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With NADPH:cytochrome P450 reductase; NADPH In water-d2; water; acetonitrile at 37℃; for 0.25h; pH=7.6; Kinetics; Concentration; Reagent/catalyst; aq. phosphate buffer; Inert atmosphere; Enzymatic reaction; |
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
In octanol at 24.84℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In octanol at 24.84℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In octanol at 24.84℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In octanol at 24.84℃; Equilibrium constant; |
A
N,N,N,N,N,N-hexamethylphosphoric triamide
B
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
In octanol at 24.84℃; Equilibrium constant; |
PhF-Al(OC(CF3)3)3
water
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
C12H2AlF27O4
Conditions | Yield |
---|---|
In fluorobenzene Schlenk technique; |
tert-butyl alcohol
A
trimethylsilyl fluoride
B
Hexamethyldisiloxane
C
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
In dichloromethane; dichloromethane-d2 at -30 - 20℃; Inert atmosphere; Schlenk technique; Glovebox; |
tert-butyldimethylsilanol
A
Hexamethyldisiloxane
B
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
C
tert-butyldimethylfluorosilane
Conditions | Yield |
---|---|
In dichloromethane; dichloromethane-d2 at -78℃; Inert atmosphere; Schlenk technique; Glovebox; |
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
nonafluoro-tert-butyl hypofluorite
Conditions | Yield |
---|---|
With fluorine; cesium fluoride at -196 - 10℃; for 3 - 4h; Inert atmosphere; | 100% |
With cesium fluoride; fluorine at -78℃; for 0.333333h; | 98% |
Stage #1: 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol With cesium fluoride at -196 - 20℃; Stage #2: With fluorine at -78℃; for 0.333333h; | 97% |
With fluorine | |
With fluorine; cesium fluoride at -78 - 20℃; under 225.023 Torr; |
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; for 0.5h; | 100% |
With sodium hydride In diethyl ether at 20℃; for 2h; Inert atmosphere; Glovebox; | 84% |
With sodium hydride In diethyl ether at 20℃; for 3h; Inert atmosphere; Glovebox; Cooling with ice; | 80% |
With sodium hydride In diethyl ether |
lithium aluminium tetrahydride
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Li[AlPFTB4]
Conditions | Yield |
---|---|
In pentane at 20℃; | 100% |
In diethyl ether; toluene for 21h; Inert atmosphere; Reflux; |
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
1,2,3,4-tetra-O-acetyl-β-D-glucopyranose
Conditions | Yield |
---|---|
Stage #1: 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol; 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose With triphenylphosphine In tetrahydrofuran at 20 - 75℃; for 0.0833333h; Inert atmosphere; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 75℃; for 3.3h; Inert atmosphere; | 99.9% |
Re(C3(OH)(C6H5)2)(CO)2(CH3C(CH2P(C6H5)2)3)
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
In dichloromethane-d2 under N2, in NMR tube; 10 equiv. of HOC(CF3)3 syringed into soln. of Re complex in CD2Cl2 cooled to -78°C (dry ice-acetone bath); not isolated; detd. by (31)P NMR spectroscopy; | 99% |
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
potassium perfluoro-tert-butoxide
Conditions | Yield |
---|---|
With potassium hydride In diethyl ether at -78 - 20℃; Inert atmosphere; | 99% |
With potassium hydroxide In ethanol at 0 - 20℃; for 0.5h; Glovebox; | 93% |
With potassium hydride In diethyl ether Inert atmosphere; Glovebox; | |
With potassium hydride In diethyl ether |
bismuth
tris-(trifluoromethyl)methyl hypochlorite
A
Bi(3+)*3(CF3)3CO(1-) = Bi{(CF3)3CO}3
B
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
byproducts: (CF3)2CO, CF3Cl, Cl2; reaction mixt. maintained at 0°C for 40 h and at room temp. for 94 h and between 25 and 30°C for 6 h; addn. of additional (CF3)3COCl; volatiles removed at room temp. under vac.; elem. anal.; | A 93% B n/a |
(trifluoromethyl)trimethylsilane
Hexafluoroacetone
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With potassium fluoride In acetonitrile Mechanism; a) 9 h, -40 deg C, b) 3 h, 18 deg C; other carbonyl compounds, variation of conditions: xfluorinated tertiary alcohols and alkoxides from nucleophilic trifluoromethylation of carbonyl compounds; | 91.3% |
With potassium fluoride In acetonitrile 1) -40 deg C, 9 h, 2) 18 deg C, 3 h; | 91.3% |
(trifluoromethyl)trimethylsilane
trifluoroacetic anhydride
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With tetramethylammonium fluoride In 1,2-dimethoxyethane at -30 - 20℃; | 87% |
1,1,1-trichloro-3,3,3-trifluoro-2-(trifluoromethyl)propan-2-ol
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With antimony pentafluoride for 3h; Heating; | 85% |
With antimony pentafluoride |
Carbonyl fluoride
(trifluoromethyl)trimethylsilane
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With potassium fluoride In acetonitrile for 18h; -40 deg C to r.t.; | 77.1% |
nanofluoro-tert-butylamine
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With trifluoroacetic acid; sodium nitrite In water at 20℃; for 1h; | 70% |
Vinylidene fluoride
C4BrF9O
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
Hexafluoroacetone
Conditions | Yield |
---|---|
at -88 - 24℃; for 12h; Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; | A n/a B n/a C 31% D n/a |
at -88 - 24℃; for 12h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; |
C4BrF9O
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
Hexafluoroacetone
Conditions | Yield |
---|---|
at -88 - 24℃; for 12h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; |
trifluorormethanesulfonic acid
B
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
bis(nonafluoro-tert-butoxy)(pentafluorophenylsulfanyl)trifluorophenylsulfur(IV)
water
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
bis(pentafluorophenyl) disulfide
C
pentafluorophenyl pentafluorobenzenethiosulfonate
Conditions | Yield |
---|---|
hydrolysis at 25°C; |
bis(nonafluoro-tert-butoxy)(trifluoromethyl)trifluoromethylsulfanylsulfur(IV)
water
A
Bis(trifluoromethyl)disulfid
B
Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester
C
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
hydrolysis at 25°C; |
nanofluoro-tert-butylamine
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
1,1,1,3,3,3-hexafluoro-2-nitroso-2-trifluoromethyl-propane
Conditions | Yield |
---|---|
With sodium nitrite In sulfuric acid At 0°C then at -10°C; | |
With NaNO2 In sulfuric acid aq. H2SO4; At 0°C then at -10°C; |
nonafluoro-tert-butyl trifluoromethanesulfinate
A
Carbonyl fluoride
B
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
C
silicon tetrafluoride
Conditions | Yield |
---|---|
byproducts: SO2; hydrolyzes in moist air at 25°C; |
CrO2{(CF3)3CO}2
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
chromic acid
Conditions | Yield |
---|---|
With water detected by NMR; |
C16H12F9NO4
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With NADPH:cytochrome P450 reductase; NADPH In water-d2; water; acetonitrile at 37℃; for 0.25h; pH=7.6; Kinetics; Concentration; Reagent/catalyst; aq. phosphate buffer; Inert atmosphere; Enzymatic reaction; |
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
In octanol at 24.84℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In octanol at 24.84℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In octanol at 24.84℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In octanol at 24.84℃; Equilibrium constant; |
A
N,N,N,N,N,N-hexamethylphosphoric triamide
B
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
In octanol at 24.84℃; Equilibrium constant; |
PhF-Al(OC(CF3)3)3
water
A
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
B
C12H2AlF27O4
Conditions | Yield |
---|---|
In fluorobenzene Schlenk technique; |
tert-butyl alcohol
A
trimethylsilyl fluoride
B
Hexamethyldisiloxane
C
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
In dichloromethane; dichloromethane-d2 at -30 - 20℃; Inert atmosphere; Schlenk technique; Glovebox; |
tert-butyldimethylsilanol
A
Hexamethyldisiloxane
B
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
C
tert-butyldimethylfluorosilane
Conditions | Yield |
---|---|
In dichloromethane; dichloromethane-d2 at -78℃; Inert atmosphere; Schlenk technique; Glovebox; |
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
nonafluoro-tert-butyl hypofluorite
Conditions | Yield |
---|---|
With fluorine; cesium fluoride at -196 - 10℃; for 3 - 4h; Inert atmosphere; | 100% |
With cesium fluoride; fluorine at -78℃; for 0.333333h; | 98% |
Stage #1: 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol With cesium fluoride at -196 - 20℃; Stage #2: With fluorine at -78℃; for 0.333333h; | 97% |
With fluorine | |
With fluorine; cesium fluoride at -78 - 20℃; under 225.023 Torr; |
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; for 0.5h; | 100% |
With sodium hydride In diethyl ether at 20℃; for 2h; Inert atmosphere; Glovebox; | 84% |
With sodium hydride In diethyl ether at 20℃; for 3h; Inert atmosphere; Glovebox; Cooling with ice; | 80% |
With sodium hydride In diethyl ether |
lithium aluminium tetrahydride
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Li[AlPFTB4]
Conditions | Yield |
---|---|
In pentane at 20℃; | 100% |
In diethyl ether; toluene for 21h; Inert atmosphere; Reflux; |
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
1,2,3,4-tetra-O-acetyl-β-D-glucopyranose
Conditions | Yield |
---|---|
Stage #1: 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol; 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose With triphenylphosphine In tetrahydrofuran at 20 - 75℃; for 0.0833333h; Inert atmosphere; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 75℃; for 3.3h; Inert atmosphere; | 99.9% |
Re(C3(OH)(C6H5)2)(CO)2(CH3C(CH2P(C6H5)2)3)
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
In dichloromethane-d2 under N2, in NMR tube; 10 equiv. of HOC(CF3)3 syringed into soln. of Re complex in CD2Cl2 cooled to -78°C (dry ice-acetone bath); not isolated; detd. by (31)P NMR spectroscopy; | 99% |
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
potassium perfluoro-tert-butoxide
Conditions | Yield |
---|---|
With potassium hydride In diethyl ether at -78 - 20℃; Inert atmosphere; | 99% |
With potassium hydroxide In ethanol at 0 - 20℃; for 0.5h; Glovebox; | 93% |
With potassium hydride In diethyl ether Inert atmosphere; Glovebox; | |
With potassium hydride In diethyl ether |
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
In hexane at -30 - 20℃; | 99% |
1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol
Conditions | Yield |
---|---|
In hexane at -30 - 20℃; | 99% |
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