Isolation of a Lewis acid-base stabilized stannanone
Mike Jörges, Daniel Knyszek, Manoj Kumar, Varre S. V. S. N. Swamy, Viktoria H. Gessner
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.
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 <svg xmlns="http://www.w3.org/2000/svg" version="1.0" width="13.200000pt" height="16.000000pt" viewBox="0 0 13.200000 16.000000" preserveAspectRatio="xMidYMid meet"><metadata> Created by potrace 1.16, written by Peter Selinger 2001-2019 </metadata><g transform="translate(1.000000,15.000000) scale(0.017500,-0.017500)" fill="currentColor" stroke="none"><path d="M0 440 l0 -40 320 0 320 0 0 40 0 40 -320 0 -320 0 0 -40z M0 280 l0 -40 320 0 320 0 0 40 0 40 -320 0 -320 0 0 -40z"/></g></svg> 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,…
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Taxonomy
TopicsSynthetic Organic Chemistry Methods · Asymmetric Synthesis and Catalysis · Oxidative Organic Chemistry Reactions