Synthesis 2020; 52(07): 1025-1034
DOI: 10.1055/s-0039-1690785
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes

Marvin Linnemannstöns
,
Beate Neumann
,
Hans-Georg Stammler
,
Norbert W. Mitzel
Universität Bielefeld, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie und Strukturchemie, Universitätsstraße 25, 33615 Bielefeld, Germany   Email: [email protected]
› Author Affiliations
This work was funded by Deutsche Forschungsgemeinschaft (DFG, grant no. Mi477/28-2, project number 271386299).
Further Information

Publication History

Received: 12 November 2019

Accepted: 06 December 2019

Publication Date:
13 January 2020 (online)


Abstract

Starting from trichloro(phenylethyl)silane, six differently fluorinated triaryl(phenylethyl)silanes were synthesized by salt elimination reactions and their structures were determined by X-ray diffraction analysis. Tris(pentafluorophenyl)(phenylethyl)silane reveals a folded structure due to intramolecular π-stacking interactions, while those with a lower degree of fluorination show either intermolecular π-stacking or no interplay between the aryl groups. A similar folded structure was observed for (4-methylphenethyl)tris(pentafluorophenyl)silane and [2-(naphth-2-yl)ethyl]tris(pentafluorophenyl)silane, both generated from the corresponding trichlorosilanes. In contrast, the inversely fluorinated [2-(pentafluorophenyl)ethyl]triphenylsilane only revealed intermolecular π-stacking interactions. Compounds with tetrafluoropyridyl substituents behave differently; with these compounds, π-stacking is only observed between the fluorinated units. All compounds were analyzed by NMR and IR spectroscopy, elemental analyses and single-crystal X-ray diffraction, and found to have strong H/C/N/F···F and N···C contacts.

Supporting Information

 
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