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Using Me 3 Si–F–Al(O R F ) 3 and Me 3 Si–Cl as Methylating Agents – Synthesis and Characterization of SeMeCl 2 [F{Al(O R F ) 3 } 2 ]
Author(s) -
Weis Philippe,
Scherer Harald,
Krossing Ingo
Publication year - 2019
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201800431
Subject(s) - yield (engineering) , chemistry , raman spectroscopy , nuclear magnetic resonance spectroscopy , nmr spectra database , salt (chemistry) , infrared spectroscopy , spectroscopy , crystallography , inorganic chemistry , nuclear chemistry , stereochemistry , spectral line , materials science , organic chemistry , physics , quantum mechanics , astronomy , optics , metallurgy
Upon reacting SeCl 4 with Me 3 Si–F–Al(OR F ) 3 , the selenonium salt SeMeCl 2 [ al‐f‐al ] ( 1 ) {[ al‐f‐al ] – = [F[Al(OC(CF 3 ) 3 ) 3 ] 2 ] – } was obtained and characterized by NMR, IR, and Raman spectroscopy as well as single crystal XRD experiments. Despite the [Se X 3 ] + ( X = F, Cl, Br, I) and [Se R 3 ] + salts ( R = aliphatic organic residue) being well known and thoroughly studied, the mixed cations are scarce. The only previous example of a salt with the [SeMeCl 2 ] + cation is SeMeCl 2 [SbCl 6 ], which was never structurally characterized and is unstable in solution over hours. Only 1 H‐NMR studies and IR spectra of this compound are known. The unexpected use of Me 3 Si–F–Al(OR F ) 3 as a methylating agent was investigated via DFT calculations and NMR experiments of the reaction solution. The reaction of SeCl 3 [ al‐f‐al ] with Me 3 Si‐Cl at room temperature in CH 2 Cl 2 proved to yield the same product with Me 3 Si–Cl acting as a methylating agent.