Nucleophilic Silylenoid Character of Stable Phosphonium Sila–ylides

Abstract

Stabilising the core: Contrary to the case of non-stabilised transient silylenes, which react with carbonyl compounds to form donor–acceptor adducts, the reaction of a phosphine-coordinated silylene with an aldehyde proceeds by a concerted [2+1] cycloaddition with a very low energy barrier to afford a pentacoordinate oxasilirane (see scheme). This result clearly demonstrates the behaviour of phosphonium sila–ylides as nucleophilic silylenoids. Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.