222046-07-3Relevant academic research and scientific papers
The synthesis and chemistry of fluorovinyl-containing phosphines and the single crystal X-ray structure of SPPr2i(CF=CF 2)
Barnes, Nicholas A.,Brisdon, Alan K.,Brown, F. R. William,Cross, Wendy I.,Crossley, Ian R.,Fish, Cheryl,Morey, James V.,Pritchard, Robin G.,Sekhri, Lakhdar
, p. 828 - 837 (2004)
The first perfluorovinyl alkyl-containing phosphines of the type PR 2(CF=CF2) (R = Et, iPr, Cy) are reported. The reactivity of these air- and moisture-stable materials has been explored, both at the phosphorus centre and at the fluorovinyl moiety. When PR 2(CX=CF2) (X = F, Cl) is reacted with LiAlH4 a mixture of PR2(CX=CFH) isomers and other defluorinated materials are produced, but the reaction with LiAlH(OBut)3 affords the single products Z-PR2(CF=CFH) or E-PR2(CCl=CFH), respectively, in high yields. Reaction of the fluorovinyl alkyl phosphines with hydrogen peroxide, elemental sulfur or selenium yields fluorovinyl-containing phosphine oxides, sulfides and selenides, respectively. The phosphine sulfide SPPr2i(CF=CF2) is the first perfluorovinyl phosphorus(v) compound to be characterised crystallographically and it exhibits an unusually short [1.9358(9) A] P=S bond. Reaction of fluorovinyl phosphines with XeF2 results in compounds of the type F 2PR2(CF=CF2), identified on the basis of multinuclear NMR studies. These compounds decompose in the presence of moisture to yield the respective phosphine oxides. Reaction of OPPh2(CF= CF2) with Br2 results in bromine addition across the double bond to give OPPh2(CFBrCF2Br).
Preparation and synthetic applications of α-fluorovinylphosphonium salts
Hanamoto, Takeshi,Kiguchi, Yasuhide,Shindo, Keiko,Matsuoka, Miki,Kondo, Michio
, p. 151 - 152 (1999)
α-Fluorovinylphosphonium salts 3 and 4 were synthesized and underwent Michael addition followed by Wittig olefination to give the corresponding monofluoroethylene compounds in good yields.
Synthesis and reactions of α-fluorovinylphosphonium salts
Hanamoto, Takeshi,Shindo, Keiko,Matsuoka, Miki,Kiguchi, Yasuhide,Kondo, Michio
, p. 103 - 107 (2007/10/03)
The α-fluorovinyltriphenylphosphonium Inflate 4 is prepared in high yields by the diphenylphosphinylation of 1,1-difluoroethylene 1 and subsequent quaternization of the phosphine 2 with diphenyliodonium triflate in the presence of CuCl. The salt 4 then undergoes Michael addition followed by Wittig olefination to give the corresponding monofluoroethylene compounds in good yields. The reaction of 4 with the caesium salts of salicylaldehyde derivatives in DMF at 130 °C affords the corresponding monofluorinated chromenes in a one-pot synthesis. The hydrolysis of 4 in the presence of sodium hydroxide gives triphenylphosphine oxide in quantitative yield. The Royal Society of Chemistry 2000.
