2264-00-8Relevant articles and documents
Highly stereoselective approach to 3-fluoroalkylated (E)-hex-3-ene-1,5- diyne derivatives via an addition-elimination reaction
Konno, Tsutomu,Kishi, Misato,Ishihara, Takashi,Yamada, Shigeyuki
, p. 144 - 151 (2013)
Palladium(0)-catalyzed Sonogashira cross-coupling reaction of 2-fluoroalkylated (Z)-2-fluoro-1-iodoethene, which is easily prepared from commercially available polyfluorinated alcohols in facile three steps, with terminal alkynes in DMF at room temperature for 24 h took place stereospecifically to give the corresponding 1-fluoroalkylated (Z)-1-fluorobut-1-en-3-yne derivatives in good to excellent yield. Thus obtained fluoroalkylated 1-fluoroenynes were effectively subjected to addition-elimination reaction with various alkynyllithiums at room temperature, leading to 3-fluoroalkylated hex-3-ene-1,5-diyne derivatives in good to high yields with an excellent E selectivity.
Synthesis of alkyl perfluoroalkanedithiocarboxylates and some aspects of their reactivity in cycloaddition reactions
Portella, Charles,Shermolovich, Yuri G.,Tschenn, Olivier
, p. 697 - 702 (2007/10/03)
A new method for the synthesis of the title compounds is proposed.The starting fluorinated compounds are commercially available trifluoroethanol and higher homologues, which were transformed in three steps into (2,2-dichloroperfluoroalkyl) alkylsulfides.The last step consisted in a substitution of chlorine by sulfur by treatment with zinc sulfide.The source of zinc sulfide is crucial and the possible role of catalytic impurities was investigated.These dithioesters are excellent dienophiles.Some cycloaddition reactions with 2,3-dimethylbuta-1,3-diene and 1-(trimethylsilyloxy)buta-1,3-diene are reported. - Keywords: perfluorinated dithioester; polyfluorinated sulfide; cycloaddition; tetrahydrothiopyran
α,α,ω-TRIHYDRO-α-HALOPERFLUOROALKANES
Shilin, S. V.,Florensova, O. N.,Chernov, N. F.,Voronkov, M. G.
, p. 1697 - 1699 (2007/10/02)
A synthesis has been developed for α,α,ω-trihydrohaloperfluoroalkanes, H(CF2CF2)n*CH2X, where X is Cl or Br and n is 1 or 4.It is based on the cleavage of the aromatic sulfonate esters of α,α,ω-trihydroperfluoroalkan-α-ols by alkali metal halides.