Bis trifluoromethyl Sulfoxide

Bis(trifluoromethyl) sulfoxide has been prepared1 previously by the direct fluorination of bis(trifluoromethyl) sulfide at —78°C. in hexafluoroethane followed by hydrolysis of the bis(trifluoro-methyl)sulfur difluoride (difluorobis(trifluoromethyl)sulfur). This method suffers because elemental fluorine must be used, and the yields are low. 

Oxidation of bis(trifluoromethyl) sulfide with commercially obtainable chlorine monofluoride in the absence of solvent yields bis(trifluoromethyl)sulfur difluoride in 90% yield.2,3 Pure bis-(trifluoromethyl)sulfur difluoride is resistant to hydrolysis and is stable in Pyrex glass at 25°C. for extended periods of time. Reaction of bis(trifluoromethyl)sulfur difluoride with anhydrous 

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A sulfoxide was obtained by oxidation of 8-[(4-trifluoromethylmercapto-phenyl)methoxy] derivative 358 with 36% H2O2 in AcOH (98MIP7) and by oxidation of l-[2-(4-thiomorfolin-l-yl)acetyl]-7-(3-methoxyphenyl)-A-methyl-A- [3,5-bis(trifluoromethyl)phenyl]ethyl -5-oxo-1,2,3,5-tetrahydro-pyrido[l,2,3-i/ ]quinoxaline-6-carboxamide with 3-chloroperbenzoic acid (01MIP12). A 7-[(4-fluorophenylsulfonyl)methyl] derivative was obtained by oxidation of a 7-[(4-fluorophenylsulfanyl)methyl]perhydropyrido[l,2-u] prazine with 3-chloroperbenzoic acid in CHCI3 (01EUP1074257). 

Sulfoxide Bis-[trifluoromethyl]-ElOa. 252 (Educt) EI0h,. 417 (SOFj + F jC-SiR2)... 

Sulfoxides can act as an S—O two-atom fragment in [4 + 2] condensations. Thus reaction of DMSO with benzoyl isocyanate in the presence of boron trifluoride etherate (75IZV1206) gives the 1,3,2,5-dioxathiazine (248). Boron trifluoride induced condensation of DMSO with N-benzoyl-S,S-bis(trifluoromethyl)sulfimide (249) gives the 1,3,2,4,5-dioxadithiazine (117) (78JA985), and the N-acylimine (250) also gives a 1,3,2,5-dioxathiazine (251) on reaction with DMSO (80ZOR463). 

DMF dmso DMSO dpae dpam dppb dppe dppm dppp ET Hdbpz Hdcmpz Hdfmpz Hdmepz Hdmpz Hdppz Hmpz Hpz Hpz Htmpz IR nbd NMR phen /V./V-Dimethylformamide Dimethyl sulfoxide (ligand) Dimethyl sulfoxide (solvent) 1.2- Bis(diphenylarsino)ethane Bis(diphenylarsino)methane 1.4- Bis(diphenylphosphino)butane 1.2- Bis(diphenylphosphino)ethane Bis(diphenylphosphino)methane 1.3- Bis(diphenylphosphino)propane Electron transfer 3.5- Di-ferf-butylpyrazole 3.5- Dicarbomethoxypyrazole 3.5- Bis(trifluoromethyl)pyrazole 3(5),4-Dimethyl-5(3)-ethylpyrazole 3.5- Dimethylpyrazole 3.5- Diphenylpyrazole 3(5)-Methylpyrazole Pyrazole A general pyrazole 3.4.5- Trimethylpyrazole Infrared spectroscopy Norbomadiene (bicyclo-[2.2.1. ]-heptadiene) Nuclear magnetic resonance 1,10-Phenanthroline... 

Ethyl 4,4,4-trifluoroacetoacetate and 3-bromo-l,l,l-trifluoroacetone react in the presence of KH in dimethyl sulfoxide at room temperature to form ethyl 2,4-bis(trifluoromethyl)4-hydroxydihydro-3-furanate (97JFC(81)123) (Scheme 68). 

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