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

Thibault Troadec 1 Morelia Lopez 1 Ricardo Rodriguez 1 Antoine Baceiredo 1 Nathalie Saffon-Merceron 2 Vicenç Branchadell 3 Tsuyoshi Kato 1
1 LHFA - Laboratoire Hétérochimie Fondamentale et Appliquée
2 ICT-FR 2599 - Institut de Chimie de Toulouse
3 UAB - Universitat Autònoma de Barcelona
Abstract : The synthesis of donor-stabilized silacyclo-butanone 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.
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https://hal.univ-brest.fr/hal-01646165
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Submitted on : Tuesday, December 5, 2017 - 2:49:07 PM
Last modification on : Monday, November 16, 2020 - 4:26:02 PM

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UNIV-BREST | CNRS | INC-CNRS | UNIV-TLSE3

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Thibault Troadec, Morelia Lopez, Ricardo Rodriguez, Antoine Baceiredo, Nathalie Saffon-Merceron, et al.. Donor-Stabilized Silacyclobutanone: A Precursor of 1-Silaketene via Retro-[2 + 2]-Cycloaddition Reaction at Room Temperature. Journal of the American Chemical Society, American Chemical Society, 2016, 138 (9), pp.2965-2968. ⟨10.1021/jacs.6b00631⟩. ⟨hal-01646165⟩

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