The curious case of a sterically crowded Stenhouse salt

We report a peculiar Stenhouse salt. It does not evolve into cyclopentenones upon basification, due to the steric hindrance of its bulky stable carbene patterns. This allowed for the observation and characterization of the transient open-chain neutral derivative, which was isolated as its cyclized f...

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Detalles Bibliográficos
Autores principales: Théry, Valentin, Molton, Florian, Sirach, Selim, Tillet, Neven, Pécaut, Jacques, Tomás-Mendivil, Eder, Martin, David
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400627/
https://www.ncbi.nlm.nih.gov/pubmed/36091895
http://dx.doi.org/10.1039/d2sc01895k
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author Théry, Valentin
Molton, Florian
Sirach, Selim
Tillet, Neven
Pécaut, Jacques
Tomás-Mendivil, Eder
Martin, David
author_facet Théry, Valentin
Molton, Florian
Sirach, Selim
Tillet, Neven
Pécaut, Jacques
Tomás-Mendivil, Eder
Martin, David
author_sort Théry, Valentin
collection PubMed
description We report a peculiar Stenhouse salt. It does not evolve into cyclopentenones upon basification, due to the steric hindrance of its bulky stable carbene patterns. This allowed for the observation and characterization of the transient open-chain neutral derivative, which was isolated as its cyclized form. The latter features an unusually long reactive C–O bond (150 pm) and a rich electrochemistry, including oxidation into an air-persistent radical cation.
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spelling pubmed-94006272022-09-08 The curious case of a sterically crowded Stenhouse salt Théry, Valentin Molton, Florian Sirach, Selim Tillet, Neven Pécaut, Jacques Tomás-Mendivil, Eder Martin, David Chem Sci Chemistry We report a peculiar Stenhouse salt. It does not evolve into cyclopentenones upon basification, due to the steric hindrance of its bulky stable carbene patterns. This allowed for the observation and characterization of the transient open-chain neutral derivative, which was isolated as its cyclized form. The latter features an unusually long reactive C–O bond (150 pm) and a rich electrochemistry, including oxidation into an air-persistent radical cation. The Royal Society of Chemistry 2022-07-27 /pmc/articles/PMC9400627/ /pubmed/36091895 http://dx.doi.org/10.1039/d2sc01895k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Théry, Valentin
Molton, Florian
Sirach, Selim
Tillet, Neven
Pécaut, Jacques
Tomás-Mendivil, Eder
Martin, David
The curious case of a sterically crowded Stenhouse salt
title The curious case of a sterically crowded Stenhouse salt
title_full The curious case of a sterically crowded Stenhouse salt
title_fullStr The curious case of a sterically crowded Stenhouse salt
title_full_unstemmed The curious case of a sterically crowded Stenhouse salt
title_short The curious case of a sterically crowded Stenhouse salt
title_sort curious case of a sterically crowded stenhouse salt
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400627/
https://www.ncbi.nlm.nih.gov/pubmed/36091895
http://dx.doi.org/10.1039/d2sc01895k
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