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Updated: Aug 6, 2026

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Facile Access to Stable Silylium Ions Stabilized by N-Heterocyclic Imines
Tatsumi Ochiai1, Tibor Szilvási2, Shigeyoshi Inoue3,4
1Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 135, Sekr. C2, 10623 Berlin, Germany. tatsumi.ochiai@mailbox.tu-berlin.de.
Abstract:
Novel silylium ions with N-heterocyclic imines were successfully synthesized. The reaction of trimethylsilyl imidazolin-2-imine Me₃SiNIPr (NIPr = bis(2,6-diisopropylphenyl)-imidazolin-2-imino) with B(C₆F₅)₃ leads to dimeric imino-substituted silylium ions through a methyl group abstraction on the silicon atom. Meanwhile, the intermolecular imino-coordinated silylium ion is formed by using the less sterically crowded imine Me₃SiNItBu (NItBu = bis(tert-butyl)-imidazolin-2-imino). Furthermore, the treatment of dimethylchlorosilane Me₂(Cl)SiNIPr with AgOTf affords the contact ion pair Me₂(OTf)SiNIPr by substitution of the chloride. A novel complex with the formula [Me₂(DMAP)SiNIPr][OTf] was prepared by coordination with 4-dimethylamino-pyridine (DMAP). In the solid state, the DMAP adduct [Me₂(DMAP)SiNIPr][OTf] contains a distinct [Me₂(DMAP)SiNIPr]⁺ moiety.
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