Isolable spirocyclic silylone: π-delocalized spiro[3.3]heptasila-2,6-diylidone

Strained cyclic tetrylones are important synthons due to various synthetic applications. Connecting two cyclic tetrylone rings through a single shared quaternary group 14 element atom to form a spirocyclic molecule has been unexplored both theoretically and experimentally. The formation of a spirocy...

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Bibliographic Details
Main Authors: Wee, Meldon Yi-Shuo, Quek, Shina, Wu, Chi-Shiun, Su, Ming-Der, So, Cheuk-Wai
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Journal Article
Language:English
Published: 2024
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Online Access:https://hdl.handle.net/10356/179284
Description
Summary:Strained cyclic tetrylones are important synthons due to various synthetic applications. Connecting two cyclic tetrylone rings through a single shared quaternary group 14 element atom to form a spirocyclic molecule has been unexplored both theoretically and experimentally. The formation of a spirocyclic motif has been a synthetic challenge. In contrast, the reaction of amidinato disilicon(I) 1, (Me3P)2SiCl4, and KC8 afforded π-delocalized spiro[3.3]heptasila-2,6-diylidone2 and tetrasilacyclobutadiene byproducts 3 and 4. Compound 2 is the smallest spirocyclic tetrylone derivative, which is composed of a σ-type lone pair and delocalized π bond in each all-silicon spirocyclic ring. The electronic property is supported by its coordination with a W(CO)5 moiety.