Safety of Tris(3,5-bis(trifluoromethyl)phenyl)phosphine. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Tris(3,5-bis(trifluoromethyl)phenyl)phosphine, is researched, Molecular C24H9F18P, CAS is 175136-62-6, about Probing steric influences on electrophilic phosphonium cations: a comparison of [(3,5-(CF3)2C6H3)3PF]+ and [(C6F5)3PF]+. Author is LaFortune, James H. W.; Szkop, Kevin M.; Farinha, Farah E.; Johnstone, Timothy C.; Postle, Shawn; Stephan, Douglas W..
The electrophilic phosphonium cation (EPC) salt [(3,5-(CF3)2C6H3)3PF][B(C6F5)4] (2) was prepared via oxidation of the precursor phosphine with XeF2 and subsequent abstraction of fluoride with [Et3Si(tol)][B(C6F5)4]. The Lewis acidity of 2 is evaluated by exptl. and computational methods and by preliminary catalysis testing. Exchange reactions of 2 and [(C6F5)3PF][B(C6F5)4] with their resp. difluorophosphoranes were studied by 2-dimensional 19F-19F NOESY/EXSY and selective 1-dimensional 19F NMR exchange spectroscopy (SEXSY) experiments affording comparative rates of fluoride exchange. Collectively, although 2 is less Lewis acidic than [(C6F5)3PF][B(C6F5)4], the improved access to the P center of 2 provides a kinetic acceleration for fluoride exchange and catalysis where the transition states are more sterically demanding.
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