Donor-Stabilized Silacyclobutanone: A Precursor of 1-Silaketene via Retro-[2 + 2]-Cycloaddition Reaction at Room Temperature

Thibault Troadec, Morelia Lopez Reyes, Ricardo Rodriguez, Antoine Baceiredo, Nathalie Saffon-Merceron, Vicenç Branchadell, Tsuyoshi Kato

Research output: Contribution to journalArticleResearchpeer-review

16 Citations (Scopus)

Abstract

© 2016 American Chemical Society. The synthesis of donor-stabilized silacyclobutanone 2 was successfully realized by the reaction of silacyclopropylidene 1 with benzaldehyde in the presence of a Lewis acid catalyst. Of particular interest, silacyclobutanone 2 evolves at room temperature via a retro-[2 + 2]-cycloaddition reaction, leading to an original NHC-stabilized 1-silaketene 4 and cis-stilbene.
Original languageEnglish
Pages (from-to)2965-2968
JournalJournal of the American Chemical Society
Volume138
Issue number9
DOIs
Publication statusPublished - 9 Mar 2016

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