3582-05-6

Basic information

• Product Name: TRIFLUOROMETHANESULFONIC ACID TRIFLUOROMETHYL ESTER
• Synonyms: methanesulfonicacid,trifluoro-,trifluoromethylester;TRIFLUOROMETHANESULFONIC ACID TRIFLUOROMETHYL ESTER;TRIFLUOROMETHYL TRIFLUOROMETHANESULFONATE;Trifluormethyl triflate;Trifluormethyl trifluoromethanesulfonate;TrifluoroMethyltriflate;Methanesulfonicacid, 1,1,1-trifluoro-, trifluoroMethyl ester
• CAS NO: 3582-05-6
• Molecular Formula: C₂F₆O₃S
• Molecular Weight: 218.08
• Mol File: 3582-05-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: -108,2°C
• Boiling Point: 21°C
• Appearance: /
• Density: 1.791 g/cm³
• Vapor Pressure: 359mmHg at 25°C
• Refractive Index: 1.297
• CAS DataBase Reference: TRIFLUOROMETHANESULFONIC ACID TRIFLUOROMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: TRIFLUOROMETHANESULFONIC ACID TRIFLUOROMETHYL ESTER(3582-05-6)
• EPA Substance Registry System: TRIFLUOROMETHANESULFONIC ACID TRIFLUOROMETHYL ESTER(3582-05-6)

Safety Data

• Statements: 14-34
• Safety Statements: 23-38
• RIDADR: 3308
• Hazardous Substances Data: 3582-05-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to pale yellow liquid

Uses

Trifluoromethyl Triflate can be used for thermal atomic layer etching processes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 4147, 1987 DOI: 10.1021/jo00228a001

InChI:InChI=1/C2F6O3S/c3-1(4,5)11-12(9,10)2(6,7)8

Synthetic route

trifluorormethanesulfonic acid (1493-13-6) → trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
With pentafluoroethanesulfonic acid anhydride at 60℃; for 4h;	100%
With phosphorus pentoxide In neat (no solvent) at 80 - 180℃; Inert atmosphere;	66%
With phosphorus pentoxide at -78 - 110℃; Inert atmosphere;	56%

trifluoromethylsulfonic anhydride (358-23-6) → trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
With trifluorormethanesulfonic acid at 180℃; for 24h; Product distribution; other temperatures and different anhydride/acid ratios;	100%
With trifluorormethanesulfonic acid at 180℃; for 24h;	100%
With trifluorormethanesulfonic acid at 80℃; for 3.3h;	97%
Stage #1: trifluoromethylsulfonic anhydride With antimony pentafluoride at -78 - 60℃; Stage #2: With potassium hydroxide at 15℃;	84%
With antimony pentafluoride

silver trifluoromethanesulfonate (2923-28-6) + methyl iodide (74-88-4) → trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
In benzene 200°C, 24 h;	86%
In benzene 200°C, 24 h;	86%

polytetrafluoroethylene (116-14-3) + Bromine(I) trifluoromethanesulfonate (70142-16-4) → Bromotrifluoromethane (75-63-8) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) + Trifluoro-methanesulfonic acid 2-bromo-1,1,2,2-tetrafluoro-ethyl ester (73323-42-9)

Conditions	Yield
at -111 - -55℃; for 10h;	A n/a B n/a C 83%

perfluoropropylene (116-15-4) + Bromine(I) trifluoromethanesulfonate (70142-16-4) → 1,2-dibromohexafluoropropane (661-95-0) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) + Trifluoro-methanesulfonic acid 2-bromo-1,1,2,3,3,3-hexafluoro-propyl ester (73323-45-2)

Conditions	Yield
at -111 - -5℃; for 24h;	A n/a B n/a C 80%

trifluoromethylsulfonic anhydride (358-23-6) → carbon tetrafluoride (75-73-0) + Trifluoromethanesulfonyl fluoride (335-05-7) + trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
With antimony pentafluoride at 25 - 60℃; for 0.25h; Yields of byproduct given;	A n/a B n/a C 80%
With antimony pentafluoride at 25 - 60℃; for 0.25h; Product distribution; Mechanism; var. Lewis acids, time, and temp.;	A n/a B n/a C 87 % Spectr.

2-(trifluoromethoxy)biphenylyl-2'-diazonium triflate → 2-(trifluoromethanesulfonyloxy)-2'-(trifluoromethoxy)biphenyl + dibenzofuran (132-64-9) + trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
In dichloromethane-d2 at 42℃; for 3h;	A 14% B 75% C n/a

perfluoroethanesulfonic acid (354-88-1) + trifluoromethylsulfonic anhydride (358-23-6) → trifluoromethyl trifluoromethanesulfonate (3582-05-6) + pentafluoroethanesulfonate de trifluoromethyle (77927-85-6)

Conditions	Yield
at 120℃; for 10h; Product distribution; other reaction temperatures and times; different anhydride/acid ratios;	A 54% B 46 % Spectr.
at 80℃; for 15h; Title compound not separated from byproducts;	A 25% B 75 % Spectr.
at 80℃; for 15h; other acid and anhydride ratio, other temperature and time;

trifluorormethanesulfonic acid (1493-13-6) + pentafluoroethanesulfonic acid anhydride (51604-58-1) → trifluoromethyl trifluoromethanesulfonate (3582-05-6) + pentafluoroethanesulfonate de trifluoromethyle (77927-85-6) + pentafluoroethyl pentafluoroethanesulfonate (77927-84-5)

Conditions	Yield
at 100℃; for 6h; Product distribution; other reaction temperatures and times; different anhydride/acid ratios;	A 44% B 44 % Spectr. C 12%

trifluorormethanesulfonic acid (1493-13-6) + fluorosulphonic acid (7789-21-1) → trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
reflux;	19%
reflux;	19%

Bromine(I) trifluoromethanesulfonate (70142-16-4) → Dichlorodifluoromethane (75-71-8) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) + perfluorochloromethyl trifluoromethanesulfonate (74501-96-5) + difluoromethyl bis(trifluoromethanesulfonate) (74512-41-7)

Conditions	Yield
at -111 - -50℃; for 15h; Further byproducts given;	A 0.6 mmol B 0.7 mmol C 0.6 mmol D 0.12 mmol

Dichlorodifluoromethane (75-71-8) + Bromine(I) trifluoromethanesulfonate (70142-16-4) → trifluoromethylsulfonic anhydride (358-23-6) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) + perfluorochloromethyl trifluoromethanesulfonate (74501-96-5) + difluoromethyl bis(trifluoromethanesulfonate) (74512-41-7)

Conditions	Yield
at -111 - -50℃; for 15h; Further byproducts given;	A 0.6 mmol B 0.7 mmol C 0.6 mmol D 0.12 mmol

trichlorofluoromethane (75-69-4) + Bromine(I) trifluoromethanesulfonate (70142-16-4) → trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
at -111 - -10℃; for 15h;	2.9 mmol

Bromotrifluoromethane (75-63-8) + Chlorine(I) trifluoromethanesulfonate (65597-24-2) → trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
at -111℃; for 1h;	3.8 mmol
at -111℃; for 1h; Product distribution; reactions of chlorine(I) and bromine(I) trifluoromethanesulfonates with various perfluoroalkyl halides;	3.8 mmol

dibromodifluoromethane (75-61-6) + Bromine(I) trifluoromethanesulfonate (70142-16-4) → trifluoromethylsulfonic anhydride (358-23-6) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) + perfluorobromomethyl trifluoromethanesulfonate (74501-92-1) + difluoromethyl bis(trifluoromethanesulfonate) (74512-41-7)

Conditions	Yield
at -111 - -60℃; for 24h; Further byproducts given;	A 0.35 mmol B 0.4 mmol C 0.7 mmol D 0.7 mmol

1,2-dibromo-1,1,2,2-tetrafluoroethane (124-73-2) + Chlorine(I) trifluoromethanesulfonate (65597-24-2) → bromopentafluoroethane (354-55-2) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) + Trifluoro-methanesulfonic acid 2-bromo-1,1,2,2-tetrafluoro-ethyl ester (73323-42-9)

Conditions	Yield
at -111 - -88℃; for 1h;	A 0.4 mmol B 0.8 mmol C 1.7 mmol

trifluorormethanesulfonic acid (1493-13-6) + pentafluoroethanesulfonate de trifluoromethyle (77927-85-6) → perfluoroethanesulfonic acid (354-88-1) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) + pentafluoroethyl pentafluoroethanesulfonate (77927-84-5)

Conditions	Yield
at 190℃; for 40h; Product distribution;

trifluorormethanesulfonic acid (1493-13-6) + pentafluoroethyl pentafluoroethanesulfonate (77927-84-5) → perfluoroethanesulfonic acid (354-88-1) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) + trifluoroacetic acid (76-05-1)

Conditions	Yield
at 190℃; for 90h; Product distribution; other perfluoroalkane sulfonic acid;

trifluorormethanesulfonic acid (1493-13-6) + pentafluoroethanesulfonic acid anhydride (51604-58-1) → trifluoromethyl trifluoromethanesulfonate (3582-05-6) + pentafluoroethanesulfonate de trifluoromethyle (77927-85-6)

Conditions	Yield
at 80℃; for 6h; other acid and anhydride ratio, other temperature and time;

trifluorormethanesulfonic acid (1493-13-6) + pentafluoroethyl pentafluoroethanepyrosulfonate de perfluoroethyle → trifluoroacetyl fluoride (354-34-7) + perfluoroethanesulfonic acid (354-88-1) + trifluoromethylsulfonic anhydride (358-23-6) + trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
at 45℃; for 14h; Product distribution;

tris(trifluoromethanesulfonyloxy)boron (64371-01-3) → Carbonyl fluoride (353-50-4) + trifluoromethylsulfonic anhydride (358-23-6) + trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
In neat (no solvent) at 200℃; for 1h;

Bromine(I) trifluoromethanesulfonate (70142-16-4) → trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
With chlorotrifluorosilane at -130 - -22℃;
thermal decompn. at 22°C;

trifluorormethanesulfonic acid (1493-13-6) → trifluoromethyl trifluoromethanesulfonate (3582-05-6) + SO2, H3PO4

Conditions	Yield
With phosphorus pentoxide other reagent;

trifluorormethanesulfonic acid (1493-13-6) + trifluoromethylsulfonic anhydride (358-23-6) → trifluoromethyl trifluoromethanesulfonate (3582-05-6) + SO2

Conditions	Yield
at 180℃; for 1h; other perfluoroalkanesulfonic anhydrides and corresponding acids, thermal stability;
at 180℃; for 1h;

trifluorormethanesulfonic acid (1493-13-6) + trifluoromethylsulfonic anhydride (358-23-6) → trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
at 176.84℃;

trifluorormethanesulfonic acid (1493-13-6) + fluorosulphonic acid (7789-21-1) → Trifluoromethanesulfonyl fluoride (335-05-7) + trifluoromethyl trifluoromethanesulfonate (3582-05-6)

trifluorormethanesulfonic acid (1493-13-6) → Carbonyl fluoride (353-50-4) + Hexafluoroethane (76-16-4) + trifluoromethylsulfonic anhydride (358-23-6) + trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
byproducts: SO3, SOF2; at 10°C;

bis(trifluoromethanesulfonyl)peroxide (4079-87-2) → Hexafluoroethane (76-16-4) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) + sulfur trioxide (7446-11-9)

Conditions	Yield
10°C;

Dichlorodifluoromethane (75-71-8) + Bromine(I) trifluoromethanesulfonate (70142-16-4) → trifluoromethyl trifluoromethanesulfonate (3582-05-6)

Conditions	Yield
in 2 : 1 mixture, -111- -50°C, 15 h;

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + 2-amino-4-methoxyphenol (20734-76-3) → 5-methoxy-3H-benzooxazol-2-one (40925-63-1)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	99%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + 3'-Amino-2'-hydroxyacetophenone (70977-72-9) → 7-acetylbenzo[d]oxazol-2(3H)-one

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	99%

2-Aminobenzyl alcohol (5344-90-1) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) → 1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one (13213-88-2)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	99%

morpholine (110-91-8) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) → morpholine-4-carbonyl fluoride (68928-13-2)

Conditions	Yield
In acetonitrile at 20℃; for 0.0333333h; Sealed tube;	99%

C3H9F2Si(1-)*C7H18N3(1+) (478945-43-6, 551925-01-0) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) → tris(dimethylamino)methylium trifluoromethanolate (1006904-67-1) + Trifluoromethanesulfonyl fluoride (335-05-7)

Conditions	Yield
In acetonitrile at -30℃;	A 98% B n/a

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + desloratadine → 4-(3-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carbonyl fluoride

Conditions	Yield
In acetonitrile at 20℃; for 0.0333333h; Sealed tube;	98%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + 4-tert-Butylaniline (769-92-6) → 1,3-bis(4-(tert-butyl)phenyl)urea (78015-86-8)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	98%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + 4-Aminoacetophenone (99-92-3) → 1,3-bis(4-acetylphenyl)urea (20782-48-3)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	98%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + 8-amino-1-naphthol (2834-91-5) → 1,3-bis(7-hydroxynaphthalen-1-yl)urea

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	97%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + 1-amino-2,3-dihydro-1H-inden-2-ol (7480-35-5, 13286-59-4, 74165-73-4, 126456-43-7, 136030-00-7, 140632-19-5, 140632-20-8) → 3,3α,8,8α-tetrahydro-2H-indeno[1,2-d]oxazol-2-one (114364-45-3)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	97%

3-cyclohexylaminopropionitrile (702-03-4) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) → (2-cyanoethyl)(cyclohexyl)carbamic fluoride

Conditions	Yield
In acetonitrile at 20℃; for 0.0333333h; Sealed tube;	97%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + amoxapine (14028-44-5) → 4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazine-1-carbonyl fluoride

Conditions	Yield
In acetonitrile at 20℃; for 0.0833333h; Sealed tube;	97%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + troxipide (30751-05-4) → 3-(3,4,5-trimethoxybenzamido)piperidine-1-carbonyl fluoride

Conditions	Yield
In acetonitrile at 20℃; for 0.0833333h; Sealed tube;	97%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + dibenzylamine (103-49-1) → N,N-dibenzylcarbamoyl fluoride

Conditions	Yield
In acetonitrile at 20℃; for 0.0333333h; Solvent; Sealed tube;	96%
In acetonitrile at 20℃; for 0.166667h; Sealed tube; Large scale;	91%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + Riluzole (1744-22-5) → 1,3-bis(6-(trifluoromethoxy)benzo[d]thiazol-2-yl)urea

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	96%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + p-toluidine (106-49-0) → 1,3-di-p-tolylurea (621-00-1)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	96%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + 4-fluoroaniline (371-40-4) → N,N'-Di-(4-Fluorphenyl)-harnstoff (370-22-9)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	96%

Thiomorpholin (123-90-0) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) → thiomorpholine-4-carbonyl fluoride

Conditions	Yield
In acetonitrile at 20℃; for 0.0833333h; Sealed tube;	95%
In acetonitrile at 20℃; for 0.0333333h; Sealed tube;	95%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + N-cyclohexyl-cyclohexanamine (101-83-7) → dicyclohexylcarbamic fluoride

Conditions	Yield
In acetonitrile at 20℃; for 0.0333333h; Sealed tube;	95%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + 4-Aminobiphenyl (92-67-1) → 1,3-di([1,1'-biphenyl]-4-yl)urea (95745-38-3)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	95%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + ethyl (E)-2-diazooct-3-enoate → ethyl (E)-4-(trifluoromethoxy)oct-2-enoate

Conditions	Yield
With silver fluoride In acetonitrile at -30 - 10℃; Inert atmosphere;	94%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + ethyl 2-diazo-3-octenoate → ethyl 4-trifluoromethoxy-2-octenoate

Conditions	Yield
With silver fluoride In acetonitrile at -30 - 10℃; Inert atmosphere;	94%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + phenethylamine (64-04-0) → 1,3-diphenethylurea (5467-84-5)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	94%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + 3,4-methylenedioxyphenylethylamine (1484-85-1) → 1,3-bis(2-(benzo[d][1,3]dioxol-5-yl)ethyl)urea

Conditions	Yield
In acetonitrile at 20℃; for 0.25h; Sealed tube;	94%

1-(2-chloro-6-fluorobenzyl)piperazine + trifluoromethyl trifluoromethanesulfonate (3582-05-6) → 4-(2-chloro-6-fluorobenzyl)piperazine-1-carbonyl fluoride

Conditions	Yield
In acetonitrile at 20℃; for 0.0333333h; Sealed tube;	94%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + Adofen (56296-78-7) → N-methyl-N-{3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl}carbamoyl fluoride

Conditions	Yield
In acetonitrile at 20℃; for 0.0333333h; Sealed tube;	94%

phenylethane 1,2-diol (93-56-1) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) → 4-Phenyl-1,3-dioxolan-2-one (4427-92-3)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 1h; Reagent/catalyst; Sealed tube;	94%

trifluoromethyl trifluoromethanesulfonate (3582-05-6) + benzylamine (100-46-9) → 1,3-dibenzylurea (1466-67-7)

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	93%

Upstream product

• 116-15-4 perfluoropropylene 
• 70142-16-4 Bromine(I) trifluoromethanesulfonate 
• 1493-13-6 trifluorormethanesulfonic acid 
• 75-05-8 acetonitrile 
• 887144-94-7 Togni's reagent II 
• 54010-75-2 zinc trifluoromethanesulfonate 
• 82113-65-3 bis(trifluoromethanesulfonyl)amide 
• 71-41-0 pentan-1-ol 
• 74-83-9 methyl bromide 
• 65597-24-2 Chlorine(I) trifluoromethanesulfonate 
• 124-73-2 1,2-dibromo-1,1,2,2-tetrafluoroethane 
• 7789-21-1 fluorosulphonic acid 
• 64371-01-3 tris(trifluoromethanesulfonyloxy)boron 
• 2794-60-7 barium trifluoromethanesulfonate 

Downstream Products

• 1493-13-6 trifluorormethanesulfonic acid 
• 77927-85-6 pentafluoroethanesulfonate de trifluoromethyle 
• 77927-84-5 pentafluoroethyl pentafluoroethanesulfonate 
• 39200-98-1 N,N'-bis(furan-2-ylmethyl)urea 
• 2298-28-4 N,N'-bis(4-hydroxyphenyl)urea 
• 17016-83-0 4-isopropyloxazolidin-2-one 
• 102-07-8 bis(diphenyl)urea 
• 1960-88-9 N,N'-bis-(4-trifluoromethylphenyl)-urea 
• 2995-45-1 1-nitro-3-(trifluoromethoxy)benzene 
• 31516-11-7 N,N'-di(2,4-dimethylphenyl)urea 
• 1234-27-1 4,4'-(carbonylbis(azanediyl))dibenzoic acid 
• 1773-43-9 4,4'-(carbonylbis(azanediyl))dibenzenesulfonamide 
• 101593-33-3 N,N'-((carbonylbis(azanediyl))bis(4,1-phenylene))diacetamide 
• 100953-84-2 N,N'-bis(4-cyanophenyl)urea 

Relevant articles and documents

Gas-phase structure and vibrational properties of trifluoromethyl trifluoromethanesulfonate, CF3SO2OCF3

Trifluoromethyl trifluoromethanesulfonate, CF3SO 2OCF3, has been synthesised and its gas-phase structure determined from electron-diffraction data. This structural study was supported by HF, MP2 and DFT (B3LYP and B1B95) calculations, which revealed a strong dependence of the theoretical structure on the polarisation of the basis set. Infrared spectra for the gas and solid and a Raman spectrum for the liquid were obtained, and the observed bands were assigned. The experimental vibrational data, along with theoretical (B3LYP) force constants, were used to define a scaled quantum mechanical force field, which enabled reproduction of the measured frequencies with a final root-mean-square deviation of 6 cm -1. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

THERMAL STABILITY OF PERFLUOROALKANESULFONIC ACIDS AND THEIR ANHYDRIDES. NEW AND EASY APPROACH TO RFSO2ORF ESTERS.

Perfluoroalkanesulfonic anhydrides (RFSO2)2O when mixed with acids decompose into perfluoroalkanesulfonic esters RFSO2ORF, thereby providing a new facile synthesis of these esters from perfluoroalkanesulfonic acids and phosphorus pentoxide.

Silver-Mediated Trifluoromethoxylation of (Hetero)aryldiazonium Tetrafluoroborates

Here we report a silver-mediated trifluoromethoxylation of (hetero)aryldiazonium tetrafluoroborates by converting an aromatic amino group into an OCF3 group. This method, which can be considered to be a trifluoromethoxylation variation of the classic Sandmeyer-type reaction, uses readily available aryl and heteroaromatic amines as starting materials and AgOCF3 as trifluoromethoxylating reagents. The broad substrate scope and simple, mild reaction condition made this transformation a valuable method in constructing aryl-OCF3 bonds.

Silver-mediated direct trifluoromethoxylation of α-diazo esters: Via the -OCF3 anion

Silver-mediated direct trifluoromethoxylation of α-diazo esters and ketosteroid was disclosed. The reactions of alkyl α-diazo arylacetates with AgOCF3 or CF3SO2OCF3/AgF at -30 to 10 °C under a N2 atmosphere provided α-trifluoromethoxyl arylacetates in up to 90% yield, while alkyl α-diazo vinylacetates reacting with CF3SO2OCF3/AgF or AgOCF3 afforded γ-trifluoromethoxyl α,β-unsaturated esters in up to 94% yield. The α-diazo ketosteroid was also trifluoromethoxylated under the standard reaction conditions. This protocol allows for an effective and convenient access to a large number of synthetic building blocks, which are promising in the development of new functional OCF3-molecules.