Isolation of an Antiaromatic 9‐Hydroxy Fluorenyl Cation

Fluorenyl cations are textbook examples of 4π electron antiaromatic five‐membered ring systems. So far, they were reported only as short‐lived intermediates generated under superacidic conditions or by flash photolysis. Attempts to prepare a m‐terphenyl acylium cation by fluoride abstraction from a...

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Autores principales: Duvinage, Daniel, Mebs, Stefan, Beckmann, Jens
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252458/
https://www.ncbi.nlm.nih.gov/pubmed/33835609
http://dx.doi.org/10.1002/chem.202100786
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author Duvinage, Daniel
Mebs, Stefan
Beckmann, Jens
author_facet Duvinage, Daniel
Mebs, Stefan
Beckmann, Jens
author_sort Duvinage, Daniel
collection PubMed
description Fluorenyl cations are textbook examples of 4π electron antiaromatic five‐membered ring systems. So far, they were reported only as short‐lived intermediates generated under superacidic conditions or by flash photolysis. Attempts to prepare a m‐terphenyl acylium cation by fluoride abstraction from a benzoyl fluoride gave rise to an isolable 9‐hydroxy fluorenyl cation that formed by an intramolecular electrophilic attack at a flanking mesityl group prior to a 1,2‐methyl shift and proton transfer to oxygen.
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spelling pubmed-82524582021-07-07 Isolation of an Antiaromatic 9‐Hydroxy Fluorenyl Cation Duvinage, Daniel Mebs, Stefan Beckmann, Jens Chemistry Communications Fluorenyl cations are textbook examples of 4π electron antiaromatic five‐membered ring systems. So far, they were reported only as short‐lived intermediates generated under superacidic conditions or by flash photolysis. Attempts to prepare a m‐terphenyl acylium cation by fluoride abstraction from a benzoyl fluoride gave rise to an isolable 9‐hydroxy fluorenyl cation that formed by an intramolecular electrophilic attack at a flanking mesityl group prior to a 1,2‐methyl shift and proton transfer to oxygen. John Wiley and Sons Inc. 2021-05-06 2021-06-01 /pmc/articles/PMC8252458/ /pubmed/33835609 http://dx.doi.org/10.1002/chem.202100786 Text en © 2021 The Authors. Published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Duvinage, Daniel
Mebs, Stefan
Beckmann, Jens
Isolation of an Antiaromatic 9‐Hydroxy Fluorenyl Cation
title Isolation of an Antiaromatic 9‐Hydroxy Fluorenyl Cation
title_full Isolation of an Antiaromatic 9‐Hydroxy Fluorenyl Cation
title_fullStr Isolation of an Antiaromatic 9‐Hydroxy Fluorenyl Cation
title_full_unstemmed Isolation of an Antiaromatic 9‐Hydroxy Fluorenyl Cation
title_short Isolation of an Antiaromatic 9‐Hydroxy Fluorenyl Cation
title_sort isolation of an antiaromatic 9‐hydroxy fluorenyl cation
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252458/
https://www.ncbi.nlm.nih.gov/pubmed/33835609
http://dx.doi.org/10.1002/chem.202100786
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