The Preparation of Organolithium Compounds by the Transmetalation Reaction. V. Perfluorovinyllithium^1-3

Structural Characterization of Hydro‐, Chloro‐ and Fluoroorganylsilanes with Substituents of Varying Electron Withdrawing Character

“…The reaction of lithium reagents 1 a – d with chlorotrimethylsilane in dimethyl ether afforded ( E )‐trimethyl(pentafluoropropen‐1‐yl)silane ( 2 a ), trimethyl(trifluoropropyn‐1‐yl)silane ( 2 b ), trimethyl(pentafluoroethyl)silane ( 2 c ) and trimethyl(trifluorovinyl)silane ( 2 d ). Because of its low boiling point of −24.8 °C [20] dimethyl ether could be easily separated from the silanes (boiling points of 2 a : 94 °C, [21] 2 b : 73–74 °C, [22] 2 c : 69–71 °C, [23] 2 d : 65 °C [10] ) whereas the purification of silanes generated in diethyl ether is sometimes effortful.…”

“…The reaction of trifluorovinyllithium with trimethylbromosilane smoothly affords trimethyl(trifluorovinyl)silane [10] which is utilized for the transfer of the trifluorovinyl group upon electrophilic compounds using catalytic amounts of fluoride [11]…”

Fluorinated stannanes

“…[4] Vinyl stannanes have also been used in the preparation of organolithium compounds by transmetalation reactions, [5] and fluorinated vinyl stannanes have recently been used in palladium-catalyzed carobonylative coupling reactions with aryl halides and triflates to yield the corresponding ketones in good yields. [6] Palladium/copper (I) halide-cocatalyzed stereospecific coupling of fluorovinylstannanes with aryl and acyl halides have also been reported [7].…”

Synthesis of the first representative of dicarbothiacyanine dyes with completely fluorinated polymethine chain

“…The preparation of stannane 2 was documented earlier in reactions of corresponding trifluorovinylmagnesium [25][26][27][28], -lithium [28] or silyle [23] reagents with Bu 3 SnCl. The scheme of stannane 2 synthesis from easy-to-access F 134a (CF 3 CHF 2 ), LiNiPr 2 , and Bu 3 SnCl at 15-20 8C is given in paper [29], but details of the procedure unfortunately are not described.…”