17170-96-6Relevant academic research and scientific papers
SYNTHESIS OF VICINAL BROMO-FLUORO ORGANIC COMPOUNDS USING ELEMENTAL FLUORINE
Brand, Michael,Rozen, Shlomo
, p. 419 - 424 (1982)
The direct action of fluorine on bromine at -78 deg C produces BrF which, without any isolation or purification, adds readily across various double bounds providing there is some hydrogen donor in the reaction mixture.Only trans addition of the elements o
Halofluorination of alkenes mediated by 1,1,3,3,3-pentafluoropropene- diethylamine adduct
Walkowiak, Justyna,Marciniak, Bartosz,Koroniak, Henryk
, p. 287 - 291,5 (2012)
1,1,3,3,3-Pentafluoropropene-diethylamine complex (PFPDEA) has been found useful as a fluoride source in halofluorination reactions of various olefins. Reactions proceeded with PFPDEA and N-halosuccinimide (NXS, X = Br, I) or 1,3-dibromo-5,5-dimethylhydan
Triethylamine Tris-hydrofluoride : A Highly Versatile Source of Fluoride Ion for the Halofluorination of Alkenes
Alvernhe, Gerard,Laurent, Andre,Haufe, Guenter
, p. 562 - 564 (1987)
The combination N-halosuccinimide/triethylamine tris-hydrofluoride is presented as a convenient reagent for halofluorination of alkenes.
Synthesis of sp 3-Enriched β-Fluoro Sulfonyl Chlorides
Gurbanov, Rustam,Sokolov, Andriy,Golovach, Sergey,Melnykov, Kostiantyn,Dobrydnev, Alexey V.,Grygorenko, Oleksandr O.
, p. 1771 - 1784 (2020/12/28)
A three-step approach to the synthesis of sp 3-enriched β-fluoro sulfonyl chlorides starting from alkenes is reported. The method was successfully applied to a wide range of acyclic and cyclic substrates, bearing either an exocyclic or an endocyclic double bond. The procedure worked with a wide range of substrates and tolerated a number of functional and protecting groups. Moreover, the target cyclic compounds were obtained as single cis diastereomers on a multigram scale. The title compounds are promising building blocks for drug discovery that can be used to obtain sp 3-enriched β-fluoro and α,β-unsaturated sulfonamides.
Halofluorination of alkenes mediated by 1,1,3,3,3-pentafluoropropene- diethylamine adduct
Walkowiak, Justyna,Marciniak, Bartosz,Koroniak, Henryk
, p. 287 - 291 (2013/01/13)
1,1,3,3,3-Pentafluoropropene-diethylamine complex (PFPDEA) has been found useful as a fluoride source in halofluorination reactions of various olefins. Reactions proceeded with PFPDEA and N-halosuccinimide (NXS, X = Br, I) or 1,3-dibromo-5,5-dimethylhydan
Halofluorination of alkenes using trihaloisocyanuric acids and HF-pyridine
Crespo, Livia T. C.,Ribeiro, Rodrigo Da S.,De Mattos, Marcio C. S.,Esteves, Pierre M.
experimental part, p. 2379 - 2382 (2010/09/04)
Halofluorination of alkenes with a new system (trihaloisocyanuric acids and HF-pyridine) results in the formation of vicinal halofluoroalkanes. The reaction is regioselective leading to Markovnikov-oriented products and the halofluorinated adducts follow anti-addition in the case of cyclohexene and 1-methylcyclohexene. Reaction yields range from 67-88%. Georg Thieme Verlag Stuttgart · New York.
Fluorination with ionic liquid EMIMF(HF)2.3 as mild HF source
Yoshino, Hideaki,Matsumoto, Kazuhiko,Hagiwara, Rika,Ito, Yasuhiko,Oshima, Koichiro,Matsubara, Seijiro
, p. 29 - 35 (2007/10/03)
Hydrogen fluoride is a basic fluorinating reagent, but handling it is difficult. For this reason, some modified fluorinating reagents such as HF-pyridine, Et3N-HF, and poly(hydrogen fluoride) complex have been developed. Those reagents, however, still require aqueous work-up procedures which generate hydrogen fluoride. Recently, ionic liquids have received much attention because of the ease in handling them and the possibility of non-aqueous work-up. An ionic liquid, 3-ethyl-1-methyimidazolium oligo hydrogen fluoride (EMIMF(HF)2.3), which is stable in air and moisture, can be used as a hydrogen fluoride equivalent for some fluorination reactions; it does not require an aqueous work-up.
A mild method for halofluorination of alkenes with ionic liquid EMIMF(HF)2.3
Yoshino, Hideaki,Matsubara, Seijiro,Oshima, Koichiro,Matsumoto, Kazuhiko,Hagiwara, Rika,Ito, Yasuhiko
, p. 121 - 123 (2007/10/03)
Halofluorination of alkene in the presence of N-halosuccinimide and ionic liquid, 3-ethyl-1-methyl-imidazorium oligo hydrogen fluoride (EMIMF(HF) 2.3), as a HF source was demonstrated. Various alkenes were converted into β-halo organofluorides
Halofluorination of alkenes with ionic liquid EMIMF(HF)2.3
Yoshino, Hideaki,Matsubara, Seijiro,Oshima, Koichiro,Matsumoto, Kazuhiko,Hagiwara, Rika,Ito, Yasuhiko
, p. 455 - 458 (2007/10/03)
Halofluorination of alkene by means of N-halosuccinimide and ionic liquid, 1-ethyl-3-methylimidazorium oligo hydrogenfluoride (EMIMF(HF)2.3), was demonstrated. Various alkenes were converted into β-halo organofluorides in good yields after non-
Generation of interhalogen fluorides under mild conditions: A comparison of sluggish and reactive interhalogen fluorides
Shellhamer, Dale F.,Horney, Mark J.,Pettus, Benjamin J.,Pettus, Tobiah L.,Stringer, Joy Merry,Heasley, Victor L.,Syvret, Robert G.,Dobrolsky Jr., John M.
, p. 1094 - 1098 (2007/10/03)
Interhalogen fluorides (XF; X = I, Br, or Cl) generated from xenon difluoride (XeF2) or triethylamine trihydrofluoride (TREAT HF) with iodine (I2), N-halosuccinimides (NXS; X = I, Br, or Cl), or alkylhypohalites (ROX; R = CH3 or t-Bu, X = Br or Cl) with alkenes and aromatics are reported. A comparison of the above reactions with other methods reported in the literature to generate interhalogen fluorides is made. Interhalogens generated from direct action of elemental fluorine (F2) or XF3 (X = I, Br, or Cl) with chlorine (Cl2), bromine (Br2), or iodine (I2) give a species that can react with electron-deficient alkenes or aromatics. These reagents are too reactive for electron-rich substrates. Interhalogen fluorides from reagents like NXS or ROX with XeF2 or amine HF are much less reactive and give good yields with electron-rich akenes or aromatics.
