The First Planar Non-Twisted Distannene

The First Planar Non-Twisted Distannene

Author: Chemistry – A European Journal

Alkenes are an important class of compounds widely used in organic synthesis. Less is known about the “heavy” analogues of alkenes, such as distannenes, which have a Sn=Sn double bond. In contrast to the planar structure of alkenes, all previously reported distannenes have a distorted structure, with either a trans-bent and/or twisted geometry around the Sn=Sn double bond (pictured below).

Dmitry Bravo-Zhivotovskii, Yitzhak Apeloig, Technion – Israel Institute of Technology, Haifa, and colleagues have synthesized the first planar non-twisted distannene, (tBu2HSi)2Sn=Sn(SiHtBu2), by mild thermolysis of (tBu2HSi)3SnH (tris(di-tert-butyl-hydridosilyl)stannane) at 70 °C in hexane. The X-ray crystallographic structure of the prepared distannene showed a planar geometry around both Sn atoms, a non-twisted Sn=Sn bond (pictured below), and the shortest known Sn=Sn bond among acyclic distannenes with a length of 2.599 Å.



This unique combination of structural properties closely resembles the structure of alkenes. The distannene exhibits reactivity that is characteristic for a Sn=Sn double bond. For example, reactions with CCl4 or 2,3-dimethylbuta-1,3-diene produce a 1,2-dichlorodistannane or a [2+4] cycloadduct, respectively. The work contributes to the understanding of the structural, spectroscopic, and bonding differences within doubly-bonded compounds of group 14 elements.


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