705-97-5Relevant academic research and scientific papers
The effect of triphenylphosphine on ring-opening of aliphatic epoxides with potassium fluoride-poly(hydrogen fluoride)
Tamura, Masanori,Shibakami, Motonari,Sekiya, Akira
, p. 147 - 149 (1997)
The ring-opening reaction of aliphatic epoxides with potassium fluoride-poly(hydrogen fluoride) is enhanced by a catalytic amount of triphenylphosphine. It is assumed that phosphonium fluoride species formed from triphenylphosphine work as fluorinating ag
Alpha selective epoxide opening with 18F-: Synthesis of 4-(3-[18F]fluoro-2-hydroxypropoxy)benzaldehyde ([ 18F]FPB) for peptide labeling
Schirrmacher, Ralf,Lucas, Philippe,Schirrmacher, Esther,W?ngler, Bj?rn,W?ngler, Carmen
scheme or table, p. 1973 - 1976 (2011/04/25)
Strained tricyclic ring systems such as epoxides are rarely used as precursors for the introduction of anionic fluorine-18 into organic compounds intended for positron emission tomography (PET). Here we report the alpha selective ring opening of epoxides
Enantioselective ring-opening of epoxides by HF-reagents: Asymmetric synthesis of fluoro lactones
Haufe, Günter,Bruns, Stefan,Runge, Martina
, p. 55 - 61 (2007/10/03)
The asymmetric ring opening of meso- and racemic-epoxides with different HF-reagents mediated by enantiopure (salen)chromium chloride provides optically active fluorohydrins with maximum 90% e.e. This reaction as well as lipase-catalyzed deracemization of
Enantioselective introduction of fluoride into organic compounds: First asymmetric ring opening of epoxides by hydrofluorinating reagents
Bruns, Stefan,Haufe, Günter
, p. 247 - 254 (2007/10/03)
The first enantioselective epoxide ring opening with hydrofluorinating agents mediated by chiral non-racemic Lewis acids is reported. The reaction of cyclohexene oxide (1) with KHF2/18-crown-6 is trans-diastereoselective and proceeds with 55% ee to form (R,R)-(-)-2-fluorocyclohexanol (2) in the presence of Jacobsen's (S,S)-(+)-(salen)chromium chloride complex A. From racemic epoxides such as styrene oxide (9) or phenyl glycidether (13), mainly or exclusively the products with fluorine in primary position are formed with 90 or 62% ee, respectively. In all cases minor amounts of corresponding chlorohydrins are formed.
Regioselectivity of the ring opening of propene oxides bearing electron-withdrawing substituents at the methyl group with Olah's reagent
Skupin, Rolf,Haufe, Guenter
, p. 157 - 165 (2007/10/03)
The regiochemistry of the hydrofluorination of terminal epoxides with Olah's reagent (Py·9HF) is dependent on the electron-withdrawing character of the β-substituents. Phenoxy ethers with different substitution patterns of the aromatic ring and several N-heterocycles were examined as β-substituents.
Regioselective conversion of O-protected glycidols to fluorohydrins catalyuzed by tetrabutylammonium dihydrogentrifluoride under solid-liquid PTC conditions
Landini, Dario,Albanese, Domenico,Penso, Michele
, p. 4163 - 4170 (2007/10/02)
A number of O-protected glycidols are regioselectively converted into the corresponding fluorohydrins FCH2CH(OH)CH2OX by reaction with catalytic amounts of Bu4N+H2F3- and a molar
TETRABUTYLAMMONIUM DIHYDROGENTRIFLUORIDE: AN EFFICIENT CATALYST FOR REGIO AND STEREOSELECTIVE CONVERSION OF EPOXIDES TO FLUOROHYDRINS UNDER SOLID-LIQUID PHASE-TRANSFER CATALYSIS CONDITIONS.
Landini, Dario,Penso, Michele
, p. 7209 - 7212 (2007/10/02)
Tetrabutylammonium dihydrogentrifluoride is an efficient and easy-to-handle hydrofluorating agent in the ring-opening reaction of oxiranes to give good or excellent yields of fluorohydrins under solid-liquid PTC conditions.
The Combination of Hydrogen Fluoride Salt and Aluminium Fluoride: an Efficient Solid Reagent for Epoxide Opening to give Fluorohydrins
Ichihara, Junko,Hanafusa, Terukiyo
, p. 1848 - 1850 (2007/10/02)
The combination of hydrogen fluoride salt and porous aluminium fluoride (MHF2-AlF3) (M = alkali metal) is a stable and efficient solid reagent for promoting the ring-opening reaction of simple aliphatic oxiranes to give the fluorohydrins under sonication,
