2338-85-4

Upstream product

• 79-38-9 Chlorotrifluoroethylene 
• 100-52-7 benzaldehyde 
• 598-73-2 1-bromo-1,2,2-trifluoroethene 
• 93629-27-7 dimethylphenyl(1,2,2-trifluoroethenyl)silane 
• 79035-75-9 1,2-bis(dimethylphenylsilyl)-1,1,2,2-tetrafluoroethane 
• 109-72-8 n-butyllithium 
• 811-97-2 1,1,1,2-tetrafluoroethane 
• 917-54-4 methyllithium 
• 594-19-4 tert.-butyl lithium 
• 212619-47-1 (Z)-2-fluoro-2-trifluoromethylethenyl tosylate 
• 683-78-3 trifluorovinyllithium 
• 186824-44-2 1,2-bis(trimethylsilyl)-1,1,2,2-tetrafluoroethane 

Downstream Products

• 55305-81-2 α-fluoro-trans-cinnamoyl fluoride 
• 66130-99-2 (Z)-2,3-difluoro-1-phenyl-2-propen-1-ol 
• 102816-92-2 (Z)-<2,3,3,3-Tetrafluoro-1-propenyl>benzene 
• 20397-59-5 ethyl (Z)-2-fluoro-3-phenylacrylate 
• 55305-87-8 α-Fluor-zimtsaeurediethylamid 
• 20397-61-9 (Z)-2-fluoro-3-phenylacrylic acid 
• 58041-00-2 (Z)-2-fluoro-3-phenylacrylaldehyde 
• 111303-10-7 ((Z)-2,3,3-Trifluoro-propenyl)-benzene 

Relevant academic research and scientific papers

Nucleophilic trifluoromethylation with organoboron reagents

Potassium trialkoxy(trifluoromethyl)borates are shown to behave as convenient reagents for nucleophilic trifluoromethylation of non-enolizable aldehydes and N-tosylimines to give CF3-substituted alcohols and N-tosylamines in good yields.

CFC- or HFC-free approach to α-substituted β,γ,γ-trifluoroallyl alcohols by the reaction of β-fluoro-β-trifluoromethylated enol tosylate with Grignard reagents

The reaction of β-fluoro-β-trifluoromethylated enol tosylate with Grignard reagents giving the corresponding β,γ,γ-trifluoroallyl alcohols as well as heteropoly acid-mediated ethanolysis of the allyl alcohols affording (Z)-β-substituted α-fluoro-α,β-unsaturated esters is described.

The reactivity of the hydrofluorocarbon 1,1,1,2-tetrafluoroethane (HFC-134a) and related compounds towards base attack. The generation and stability of the tetrafluoroethyl, trifluorovinyl and related anions

Trifluorovinyllithium (CF2 = CFLi) has been successfully synthesised from 1,1,1,2-tetrafluoroethane using n-butyllithium at -78°C in ether. Other bases (LDA, DBU, MeLi, t-BuLi, t-BuOK) were tried with varied success. The stability of the system was dependent on temperature, concentration and solvent system employed. 1-Chloro-2,2,2-trifluoroethane (133a) led to an analogous polyfluorovinyllithium, but 1,1,1-trifluoro- and 1,1,1,2,2,2-hexafluoro- ethane did not.

Preparation of and fluoroalkylation with (chlorodifluoromethyl)trimethylsilane, difluorobis(trimethylsilyl)methane, and 1,1,2,2-tetrafluoro-1,2-bis(trimethylsilyl)ethane

CF2BrCl reacts with aluminum/N-methylpyrrolidinone in the presence of chlorotrimethylsilane to give Me3SiCF2Cl in high yield. Similarly, CF2Br2 gives Me3SiCF2Br with bromotrimethylsilane. Chlorodifluoromethylation of aldehydes using Me3SiCF2Cl and a catalytic amount of TBAF in polar solvents occurs at room temperature, providing difluoromethylated alcohols in two steps. Electroreduction of Me3SiCF2Cl in the presence of chlorotrimethylsilane gives Me3SiCF2SiMe3 (anion-derived product) and Me3SiCF2CF2SiMe3 (radical-derived product). Using THF/HMPA strongly favors the former, whereas THF/TDA-1 (tris(3,6-dioxaheptyl)amine) the latter. Me3SiCF2SiMe3 difluoromethylates aldehydes acting as a difluoromethylene dianion ('CF22-'/equivalent), whereas Me3SiCF2CF2SiMe3 acts at room temperature as an in situ source for the perfluorovinyl anion (due to β-elimination of fluorotrimethylsilane). However, at low temperature the elimination pathway is suppressed and tetrafluoroethylene dianion ('-CF2CF2-'/equivalent) behavior is observed. The structure of Me3SiCF2CF2SiMe3 was analyzed by X-ray diffraction. All of the studied fluoroalkylating reagents are moisture- and air-stable and can be readily obtained from a single convenient precursor (CF2BrCl).

1,2-Bis(dimethylphenylsilyl)tetrafluoroethane. Application to the trifluorovinylation and tetrafluoroethylenation of carbonyl compounds

The reaction of 1,2-bis(dimethylphenylsilyl)tetrafluoroethane with a small excess of benzaldehyde in the presence of the promoter gave the trifluorovinylated product, 1,1,2-trifluoro-3-phenylpropen-3-ol, selectively. The tetrafluoroethylenated product, 2,2,3,3-tetrafluoro-1,4-diphenylbutane-1,4-diol, was also obtained in benzaldehyde solvent or at low temperatures.

The hydrofluorocarbon 1,1,1,2-tetrafluoroethane (HFC-134a) as a ready source of trifluorovinyllithium

Trifluorovinyllithium has been synthesised in high yield from 1,1,1,2-tetrafluoroethane (HFC 134a) by treatment with butyllithium at -78°C, and then treated with a variety of electrophiles in one-pot reactions.

Fluoride Ion-Catalyzed Generation and Carbonyl Addition of α-Halo Carbanions Derived from α-Halo Organosilicon Compounds

The title carbanion species are generated from the corresponding α-haloorganosilicon compounds by the action of a catalytic amount of tris(diethylamino)sulfonium difluorotrimethylsilicate and are found to undergo addition to aldehyde carbonyl efficiently at ambient temperature.The synthetic potential of the reaction is demonstrated by application to the synthesis of some insecticides.

Hydrogen Fluoride/Tetrahydrofuran as a Fluorinating Medium. A General Synthesis of 1,1,1,2-Tetrafluoro-2-alkenes

A general and simple two step synthesis of 1,1,1,2-tetrafluoro-2-alkenes is presented.The key step is the rearrangement-conversion of 1,1,2-trifluoro-1-alken-3-ols under the influence of hydrogen fluoride/tetrahydrofuran (5:1) as a fluorinating medium.