Related Experiment Video
Updated: Apr 28, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Dihydrogen activation by a silylium silylene frustrated Lewis pair and the unexpected isomerization reaction of a
Annemarie Schäfer1, Matti Reißmann, André Schäfer
1Carl von Ossietzky-Universität Oldenburg, Fakultät V Institut für Chemie, Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg (Germany). thomas.mueller@uni-oldenburg.de.
Abstract:
The isolable silylene 1 forms a frustrated Lewis pair with silylium ion 2 that is able to split hydrogen under ambient conditions. The protonated silylene 3 obtained in this reaction isomerizes to yield the hydrogen-bridged disilyl cation 4. Cation 4 is fully characterized by NMR spectroscopy and by XRD analysis. Its formation via the protonated silylene 3 is indicated by independent synthesis of cation 3 by hydride abstraction from the corresponding dihydridosilane 11 and is further supported by the results of density functional calculations.
Related Concept Videos
Diels–Alder Reaction: Characteristics of Dienes
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Preparation and Reactions of Sulfides

