The First Planar, Not Twisted, Distannene - A Structural Alkene Analog. Synthesis, Isolation and X-ray Crystallography Characterization

Roman Bashkurov; Natalia Fridman; Dmitry Bravo-Zhivotovskii; Yitzhak Apeloig

doi:10.1002/chem.202302678

The First Planar, Not Twisted, Distannene - A Structural Alkene Analog. Synthesis, Isolation and X-ray Crystallography Characterization

Chemistry. 2023 Dec 11;29(69):e202302678. doi: 10.1002/chem.202302678. Epub 2023 Oct 20.

Authors

Roman Bashkurov¹, Natalia Fridman¹, Dmitry Bravo-Zhivotovskii¹, Yitzhak Apeloig¹

Affiliation

¹ Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa, 32000, Israel.

PMID: 37675971
DOI: 10.1002/chem.202302678

Abstract

The tetrasilyl-substituted distannene, (tBu₂ HSi)₂ Sn=Sn(SiHtBu₂ )₂ 6, was synthesized by mild thermolysis (70 °C in hexane) of tris(di-tert-butyl-hydridosilyl)stannane 4. The X-ray crystallography structure of 6 reveals the following unusual structural properties: a planar geometry around both Sn atoms (Σ∡Sn=359.87°), a non-twisted Sn=Sn double bond, and the shortest Sn=Sn double bond of 2.599 Å among all acyclic distannenes. Thus, compound 6 is the first reported distannene having a structure closely analogous to a classic alkene. Reactions of 6 with CCl₄ or with 2,3-dimethylbuta-1,3-diene to produce 1,2-dichlorodistannane 9 and the [2+4] cycloadduct 10, respectively, are characteristic for a Sn=Sn double bond.

Keywords: distannene; double bond; group 14 elements; stannylene; tin.