Abstract
Silylation of N-(2-hydroxyethyl)imidazole, HOCH2CH2Im (1), with hexamethyldisilazane gave N-(2-trimethylsilyloxyethyl)imidazole, Me3SiOCH2CH2Im (2), which underwent quaternization reactions with the alkyl halides and gave three new N-(trimethylsilyloxyethyl) imidazolium halides, Me3SiOCH2CH2Im+RX-, where Im+ = imidazolium and R/X = Me/I (3), CH2CH2F/Br (4), and CH2CH2CF3/I (5). The ethyl ether, 6, formed from 1 and ethyl bromide was quaternized with CF3CH2CH2I to obtain 7, followed by anion exchange with LiN(SO2CF3)2 to obtain 8. The metathesis reactions of 3−5 with cyanuric fluoride in acetonitrile at 25 °C gave tris[2-(N‘-alkylimidazolium)ethoxy] triazine trihalides, N3C3(OCH2CH2Im+RX-)3, where R/X = Me/I (9), CH2CH2F/Br (10), and CH2CH2CF3/I (11). Two neutral trimeric compounds, N3C3(OCH2CH2Im)3 (12) and N3C3(OCH2CH2NMe2)3 (14), were prepared from reactions of cyanuric fluoride and Me3SiOCH2CH2NMe2 (13), or 2, respectively. The quaternization of 12 with MeI gave tris[oxoethyl(trimethyl)ammonium]triazin...
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