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

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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Chimie organique

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https://hal.univ-brest.fr/hal-01646165

Soumis le : mardi 5 décembre 2017-14:49:07

Dernière modification le : jeudi 18 juillet 2024-10:51:05

Dates et versions

hal-01646165 , version 1 (05-12-2017)

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HAL Id : hal-01646165 , version 1
DOI : 10.1021/jacs.6b00631

Citer

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, 2016, 138 (9), pp.2965-2968. ⟨10.1021/jacs.6b00631⟩. ⟨hal-01646165⟩

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