NHC·Alane Adducts as Hydride Sources in the Hydrodefluorination of Fluoroaromatics and Fluoroolefins was written by Schneider, Heidi;Hock, Andreas;Jaeger, Alma D.;Lentz, Dieter;Radius, Udo. And the article was included in European Journal of Inorganic Chemistry in 2018.Computed Properties of C5F5N The following contents are mentioned in the article:
The authors present herein the use of NHC-stabilized alane adducts of the type (NHC)·AlH3 [NHC = Me2Im , Me2ImMe , iPr2Im, iPr2ImMe, Dipp2Im] and (NHC)·AliBu2H [NHC = iPr2Im , Dipp2Im ] as novel hydride transfer reagents in the hydrodefluorination (HDF) of different fluoroaroms. and hexafluoropropene. Depending on the alane adduct used, HDF of pentafluoropyridine to 2,3,5,6-tetrafluoropyridine in yields of 15-99% was observed The adducts (Me2Im)·AlH3, (Me2ImMe)·AlH3 , and (Dipp2Im)·AlH3 achieved a quant. conversion into 2,3,5,6-tetrafluoropyridine at room temperature immediately after mixing the reactants. Studies on the HDF of fluorobenzenes with the (NHC)·AlH3 adducts and (Dipp2Im)·AliBu2H showed the decisive influence of the reaction temperature on the H/F exchange and that 135° in xylene afforded the best product distribution. Although the HDF of hexafluorobenzene yielded 1,2,4,5-tetrafluorobenzene in moderate yields with traces of 1,2,3,4-tetrafluorobenzene and 1,2,4-trifluorobenzene, pentafluorobenzene was converted quant. into 1,2,4,5-tetrafluorobenzene, with (Dipp2Im)·AliBu2H showing the highest activity and reaching complete conversion after 12 h at 135° in xylene. The HDF of hexafluoropropene with (Me2Im)·AlH3 occurred even at low temperatures and preferably at the CF2 group with the formation of 1,2,3,3,3-pentafluoropropene (with 0.4 equiv of 1) or 2,3,3,3-tetra-fluoropropene (with 0.9 equiv of 1) as the main product. This study involved multiple reactions and reactants, such as 2,3,4,5,6-Perfluoropyridine (cas: 700-16-3Computed Properties of C5F5N).
2,3,4,5,6-Perfluoropyridine (cas: 700-16-3) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Computed Properties of C5F5N