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

doi:10.1021/jacs.6b00631

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 journal › Article › Research › peer-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 language	English
Pages (from-to)	2965-2968
Journal	Journal of the American Chemical Society
Volume	138
Issue number	9
DOIs	https://doi.org/10.1021/jacs.6b00631
Publication status	Published - 9 Mar 2016

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Troadec, T., Lopez Reyes, M., Rodriguez, R., Baceiredo, A., Saffon-Merceron, N., Branchadell, V., & Kato, T. (2016). Donor-Stabilized Silacyclobutanone: A Precursor of 1-Silaketene via Retro-[2 + 2]-Cycloaddition Reaction at Room Temperature. Journal of the American Chemical Society, 138(9), 2965-2968. https://doi.org/10.1021/jacs.6b00631

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abstract = "{\textcopyright} 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.",

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Donor-Stabilized Silacyclobutanone: A Precursor of 1-Silaketene via Retro-[2 + 2]-Cycloaddition Reaction at Room Temperature. / Troadec, Thibault; Lopez Reyes, Morelia; Rodriguez, Ricardo; Baceiredo, Antoine; Saffon-Merceron, Nathalie; Branchadell, Vicenç; Kato, Tsuyoshi.

In: Journal of the American Chemical Society, Vol. 138, No. 9, 09.03.2016, p. 2965-2968.

Research output: Contribution to journal › Article › Research › peer-review

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AB - © 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.

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