# Isolation of a Lewis acid-base stabilized stannanone

## TL;DR

Scientists isolated a stannanone stabilized by a Lewis acid, revealing a highly polarized and reactive Sn–O bond.

## Contribution

The first isolation of a diylide-substituted stannanone stabilized by a Lewis acid-base interaction.

## Key findings

- A monomeric stannanone was isolated using a thiophosphinoyl-substituted ylide.
- The Sn–O bond is short but highly polarized with negligible π-contribution.
- The bond shows high reactivity toward cleavage due to opposing charges.

## Abstract

A diylide-substituted stannanone, stabilized by the Lewis acid SnCl2 (formally written as Y2Sn

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O → SnCl2) has been successfully isolated and characterized by spectroscopic, crystallographic and computational methods. The nature of the ylide substituent proved critical for its successful isolation. While oxidation of a stannylene with a cyano-substituted ylide yielded only a dimeric stannoxane, incorporation of a thiophosphinoyl moiety provided sufficient steric bulk and additional stabilization through PS coordination, enabling the isolation of the monomeric stannanone. Computational studies revealed a strongly polarized Sn–O bond with negligible π-contribution to the bonding interaction and high opposing charges, resulting in a short Sn–O linkage but a high reactivity toward bond cleavage. This study highlights the challenge associated with stabilizing formal multiple bonds with the heavier atoms and underscores the importance of substituent design in achieving such stabilization.

A diylide-substituted Lewis acid-base stabilized stannanone was successfully isolated. Experimental and computational studies revealed a short, but highly polarized Sn–O bond with negligible π-contribution and high reactivity toward bond cleavage.