6719-70-6Relevant articles and documents
Inter- and Intramolecular Aryl–Aryl Interactions in Partially Fluorinated Ethylenedioxy-bridged Bisarenes**
Weddeling, Jan-Henrik,Vishnevskiy, Yury V.,Neumann, Beate,Stammler, Hans-Georg,Mitzel, Norbert W.
supporting information, p. 16111 - 16121 (2020/10/28)
Several ethylenedioxy-bridged bisarenes with a variety of type and number of aryl groups were synthesized to study non-covalent dispersion-driven inter- and intramolecular aryl–aryl interactions in the solid state and gas phase. Intramolecular interactions are preferably found in the gas phase. DFT calculations with and without dispersion correction show larger interacting aromatic groups increase the stabilization energy of folded conformers and decrease the intermolecular centroid–centroid distance. Single-molecule structures generally adopt folded conformations with short intramolecular aryl–aryl contacts. Gas electron diffraction experiments were performed exemplarily for 1-(pentafluorophenoxy)-2-(phenoxy)ethane. A new procedure for structure refinement was developed to deal with the conformational complexity of such molecules. The results are an experimental confirmation of the existence of folded conformations of this molecule with short intramolecular aryl–aryl distances in the gas phase. Solid-state structures are dominated by stretched structures without intramolecular aryl–aryl interactions but interactions with neighboring molecules.
REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. XI. REACTIONS OF HEXAFLUOROBENZENE WITH THE SODIUM SALTS OF ETHYLENE GLYCOL AND AMINO- AND MERCAPTOETHANOL
Kizner, T. A.,Shteingarts, V. D.
, p. 2183 - 2188 (2007/10/02)
In the reaction of hexafluorobenzene with sodium ethylene glycolate in liquid ammonia at -40 to 33 deg C 1,2-di(pentafluorophenoxy)ethane and (with an excess of the reagent) 6,7,9,10,16,17,19,20-octafluoro-1,4,11,14-tetraoxaparacyclophane are formed with almost quantitative yields.The reaction of hexafluorobenzene with the sodium salt of aminoethanol under the same conditions gave β-aminoethoxypentafluorobenzene, while the action both of mercaptoethanol itself and of its sodium salt led to substitution of the two para-oriented fluorine atoms by β-hydroxyethylthio groups.