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

Department of Chemistry

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

34 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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10.1021/jacs.6b00631

CCDC 1443337: Experimental Crystal Structure Determination
Troadec, T. (Creator), Lopez Reyes, M. (Contributor), Rodriguez, R. (Creator), Baceiredo, A. (Creator), Saffon-Merceron, N. (Creator), Branchadell, V. (Creator) & Kato, T. (Creator), Cambridge Crystallographic Data Centre, 18 Dec 2015
DOI: 10.5517/ccdc.csd.cc1kfx85, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1kfx85&sid=DataCite
Dataset
CCDC 1443340: Experimental Crystal Structure Determination
Troadec, T. (Creator), Lopez Reyes, M. (Contributor), Rodriguez, R. (Creator), Baceiredo, A. (Creator), Saffon-Merceron, N. (Creator), Branchadell, V. (Creator) & Kato, T. (Creator), Cambridge Crystallographic Data Centre, 18 Dec 2015
DOI: 10.5517/ccdc.csd.cc1kfxc8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1kfxc8&sid=DataCite
Dataset
CCDC 1443339: Experimental Crystal Structure Determination
Troadec, T. (Creator), Lopez Reyes, M. (Contributor), Rodriguez, R. (Creator), Baceiredo, A. (Creator), Saffon-Merceron, N. (Creator), Branchadell, V. (Creator) & Kato, T. (Creator), Cambridge Crystallographic Data Centre, 18 Dec 2015
DOI: 10.5517/ccdc.csd.cc1kfxb7, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1kfxb7&sid=DataCite
Dataset

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

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.",

author = "Thibault Troadec and {Lopez Reyes}, Morelia and Ricardo Rodriguez and Antoine Baceiredo and Nathalie Saffon-Merceron and Vicen{\c c} Branchadell and Tsuyoshi Kato",

year = "2016",

month = mar,

day = "9",

doi = "10.1021/jacs.6b00631",

language = "English",

volume = "138",

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T1 - Donor-Stabilized Silacyclobutanone: A Precursor of 1-Silaketene via Retro-[2 + 2]-Cycloaddition Reaction at Room Temperature

AU - Troadec, Thibault

AU - Lopez Reyes, Morelia

AU - Rodriguez, Ricardo

AU - Baceiredo, Antoine

AU - Saffon-Merceron, Nathalie

AU - Branchadell, Vicenç

AU - Kato, Tsuyoshi

PY - 2016/3/9

Y1 - 2016/3/9

N2 - © 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.

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.

U2 - 10.1021/jacs.6b00631

DO - 10.1021/jacs.6b00631

M3 - Article

SN - 0002-7863

VL - 138

SP - 2965

EP - 2968

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 9

ER -

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

Abstract

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Datasets

CCDC 1443337: Experimental Crystal Structure Determination

CCDC 1443340: Experimental Crystal Structure Determination

CCDC 1443339: Experimental Crystal Structure Determination

Cite this