85914-80-3

Upstream product

• 100-52-7 benzaldehyde 
• 186824-44-2 1,2-bis(trimethylsilyl)-1,1,2,2-tetrafluoroethane 
• 79035-75-9 1,2-bis(dimethylphenylsilyl)-1,1,2,2-tetrafluoroethane 
• 71-43-2 benzene 

Downstream Products

• 2525-85-1 2,2,3,3-tetrafluoro-1,4-diphenylbutane-1,4-dione 

Relevant academic research and scientific papers

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.

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).

REDUCTION OF POLYFLUORINATED CARBONYL COMPOUNDS BY ETHOXYMAGNESIUM BROMIDE

The reduction of perfluoroalkyl phenyl ketones and diketones with ethoxymagnesium bromide takes place readily in the absence of branching at the α-carbon atom of the aliphatic radical and in the absence of a substituent or in the presence of only one orth