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• W2045380964 abstract "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)." @default.
• W2045380964 created "2016-06-24" @default.
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• W2045380964 date "1997-02-01" @default.
• W2045380964 modified "2023-10-14" @default.
• W2045380964 title "Preparation of and Fluoroalkylation with (Chlorodifluoromethyl)trimethylsilane, Difluorobis(trimethylsilyl)methane, and 1,1,2,2-Tetrafluoro-1,2-bis(trimethylsilyl)ethane" @default.
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• W2045380964 doi "https://doi.org/10.1021/ja962990n" @default.
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