The stereospecific preparation of two perfluoro-1,3-butadiene synthons; (E)-1-trimethylsilyl-1,2,3,4,4-pentafluoro-1,3-butadiene and (E)-1-tributylstannyl-1,2,3,4,4-pentafluoro-1,3-butadiene

Fluorinated stannanes

“…19 F NMR analysis of the solution indicated conversion of the stannane to 1,1,2-trifluoro-2-iodoethene. 19 F NMR (CDCl 3 ): d À90.4 (dd, 2 J FF ¼ 68:9 Hz, 3 J FFðcisÞ ¼ 47:6 Hz, 1F); À115.5 (dd, 3 J FFðtransÞ ¼ 129:0 Hz, 2 J FF ¼ 68:9 Hz, 1F); À151.1 (dd, 3 J FFðtransÞ ¼ 129:1 Hz, 3 J FFðcisÞ ¼ 47:5 Hz, 1F) [27].…”

The preparation of perfluoroalkenyl allenes (trienes) and pentafluorophenyl allenes

“…The appropriate vinyliodide, trifluorovinyliodide [14] or (Z)-pentafluoropropenyliodide [15] (50 mmol) was then added dropwise to the solution. After approximately one-third of the vinyliodide had been added, an exotherm occurred, which was controlled by the rate of addition of the remaining vinyliodide.…”

Functionalized fluoroalkyl and alkenyl silanes: Preparations, reactions, and synthetic applications

“…Deprotonation of (E)-1,2-difluoroethenylsilane 233 with lithium amide followed by stannylation gives (Z)-(1,2-difluoro-2-trimethylsilyl)ethenyl(tributyl)stannane 234. Pd-catalyzed cross-coupling of 234 with trifluoroiodoethene synthesizes perfluorobutadienylsilane 235 (Scheme 59) [84].…”