Issue 19, 2024

A tin analogue of propadiene with cumulated C[double bond, length as m-dash]Sn double bonds

Abstract

The synthesis, structure, and properties of a stable, linear 2-stannapropadiene are reported. The identical C[double bond, length as m-dash]Sn bonds in this 2-stannapropadiene are the shortest hitherto reported C–Sn bonds. This 2-stannapropadiene features a 119Sn NMR signal at 507 ppm for the central tin atom, indicative of an unsaturated Sn4+ oxidation state. Due to the inert-pair effect, the tin atom displays a pronounced preference for the +2 oxidation state over the +4 oxidation state. Nevertheless, by employing silyl substituents, it is possible to disrupt the inert-pair effect, leading to the formation of an isolable 2-stannapropadiene with a linear structure centered on a Sn4+ atom. Treatment of this 2-stannapropadiene with SnBr2·dioxane resulted in the formation of a novel four-membered cyclic 1,1-dibromo-1,3-distannetane, which was subsequently reduced to afford the corresponding stable four-membered cyclic bis(stannylene).

Graphical abstract: A tin analogue of propadiene with cumulated C [[double bond, length as m-dash]] Sn double bonds

Supplementary files

Article information

Article type
Edge Article
Submitted
05 Jan 2024
Accepted
25 Mar 2024
First published
02 Apr 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 7072-7078

A tin analogue of propadiene with cumulated C[double bond, length as m-dash]Sn double bonds

K. Sugamata, T. Asakawa and M. Minoura, Chem. Sci., 2024, 15, 7072 DOI: 10.1039/D4SC00093E

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