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Tris(dimethylamino)silylium ion: structure and reactivity of a dimeric silaguanidinium

Abstract

Although several strategies for the stabilization of silylium ions have been established, the “π-stabilization” by directly attached π-donor heteroatoms at silicon has not been developed yet. Hydride abstraction from (Me2N)3SiH generates dicationic [(Me2N)3Si+]2 in solution and in the solid state – constituting the dimer of an elusive silaguanidinium ion. The compound can be synthesized on gram scale and is compatible with common organic solvents. However, it readily undergoes spontaneous electrophilic silylation of electron-rich aromatic compounds or initiates a catalytic hydrodefluorination reaction.

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Publication details

The article was received on 10 May 2019, accepted on 11 Jun 2019 and first published on 12 Jun 2019


Article type: Communication
DOI: 10.1039/C9CC03625C
Chem. Commun., 2019, Accepted Manuscript

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    Tris(dimethylamino)silylium ion: structure and reactivity of a dimeric silaguanidinium

    N. Kramer, H. Wadepohl and L. Greb, Chem. Commun., 2019, Accepted Manuscript , DOI: 10.1039/C9CC03625C

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