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Molecules 2016, 21(9), 1155; doi:10.3390/molecules21091155

Facile Access to Stable Silylium Ions Stabilized by N-Heterocyclic Imines

Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 135, Sekr. C2, 10623 Berlin, Germany
Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szent Gellért tér 4, 1111 Budapest, Hungary
Department of Chemistry, Catalysis Research Center and Institute of Silicon Chemistry, Technische Universität München, Lichtenbergstraße 4, 85748 Garching, Germany
Author to whom correspondence should be addressed.
Academic Editor: Mitsuo Kira
Received: 26 July 2016 / Revised: 23 August 2016 / Accepted: 25 August 2016 / Published: 30 August 2016
(This article belongs to the Special Issue Advances in Silicon Chemistry)
View Full-Text   |   Download PDF [2665 KB, uploaded 30 August 2016]   |  


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. View Full-Text
Keywords: silylium; imine; cation; silicon; borate silylium; imine; cation; silicon; borate

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Ochiai, T.; Szilvási, T.; Inoue, S. Facile Access to Stable Silylium Ions Stabilized by N-Heterocyclic Imines. Molecules 2016, 21, 1155.

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