803-13-4

Upstream product

• 354-64-3 Pentafluoroethyl iodide 
• 1064-10-4 hexaphenylditin 
• 42393-72-6 (C₆H₅)3SnCH₂CH₂N(CH₃)C₆H₅ 
• 42393-74-8 (C₆H₅)3SnCH₂CH₂N(C₆H₅)2 
• 201741-99-3 triphenyl-trityl stannane 
• 639-58-7 triphenyltin chloride 
• 4167-90-2 lithium triphenylstannide 
• 354-33-6 1,1,1,2,2-pentafluoroethane 
• 91935-83-0 (Pentafluoroethyl)lithium 

Downstream Products

• 71-43-2 benzene 

Relevant academic research and scientific papers

Synthesis of Mono-, Bis- and Tris(pentafluoroethyl)tin Derivatives, (C2F5)4?nSnXn (X=Ph, Me, Cl, Br, Cp; n=1–3)

For (pentafluoroethyl)phenylstannanes, (C2F5)4?n SnPhn (n=1–3), and dimethylbis(pentafluoroethyl)stannane, (C2F5)2SnMe2, a high yield synthesis was developed by the use of LiC2F5 as a C2F5 transfer reagent. The treatment of these products with gaseous hydrogen chloride or hydrogen bromide afforded (C2F5)4?nSnXn (X=Cl, Br; n=1–3) in good yields. The (pentafluoroethyl)stannanes were fully characterized by 1H, 13C, 19F and 119Sn NMR, IR spectroscopy and mass spectrometry. The treatment of the (pentafluoroethyl)tin halides (C2F5)4?nSnXn with 1,10-phenanthroline (phen) led to the formation of the corresponding octahedrally coordinated complexes [(C2F5)4?nSnXn(phen)], the structures of which were elucidated by X-ray diffraction analyses. The bromostannane (C2F5)3SnBr reacted with sodium cyclopentadienide to give the (η1-cyclopentadienyl)tris(pentafluoroethyl)stannane, (C2F5)3SnCp, for which single-crystal X-ray diffraction analysis could be performed. The coupling constants 1J(119Sn,13C) and 2J(119Sn,19F) of all new stannanes are strongly correlated and sensitive to the substitution pattern at the tin atom. For both coupling constants a negative sign could be assigned.

On Pentakis(pentafluoroethyl)stannate, [Sn(C2F5)5]?, and the Gas-Free Generation of Pentafluoroethyllithium, LiC2F5

Pentafluoroethyllithium, LiC2F5, has been established as an efficient and versatile reagent for the transfer of the pentafluoroethyl unit to a number of electrophiles. Here, the stability of this species up to ?40 °C is of advantage, particularly in comparison to its smaller congener LiCF3. The usual production of LiC2F5, however, from gaseous HC2F5 or IC2F5 and strong bases requires specially designed apparatuses, which severely impeded its value as a laboratory reagent. In this contribution we communicate an alternative gas-free and highly efficient protocol for the synthesis of LiC2F5 from the already commercialized stannate salt [PPh4][Sn(C2F5)5]. The [Sn(C2F5)5]? anion represents not only the first example of a structurally characterized hypervalent pentaalkylstannate but also serves as a precursor for the synthesis of the homoleptic tetrakis(pentafluoroethyl)stannane, Sn(C2F5)4. The reaction of the latter with n-butyllithium provides an insight into the mechanism of LiC2F5 generation.