Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride

A novel reactivity of 1,1,1-trifluoroalkanones is reported, where the reaction with AlCl(3) results in the formation of 1,1-dichloro-1-alkenones. The reaction scope was found to be broad, with various chain lengths and aryl substituents tolerated. For substrates containing an electron-rich aromatic...

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Autores principales: Lansbergen, Beatrice, Meister, Catherine S, McLeod, Michael C
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7884876/
https://www.ncbi.nlm.nih.gov/pubmed/33633808
http://dx.doi.org/10.3762/bjoc.17.36
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author Lansbergen, Beatrice
Meister, Catherine S
McLeod, Michael C
author_facet Lansbergen, Beatrice
Meister, Catherine S
McLeod, Michael C
author_sort Lansbergen, Beatrice
collection PubMed
description A novel reactivity of 1,1,1-trifluoroalkanones is reported, where the reaction with AlCl(3) results in the formation of 1,1-dichloro-1-alkenones. The reaction scope was found to be broad, with various chain lengths and aryl substituents tolerated. For substrates containing an electron-rich aromatic ring, further reactions take place, resulting in bicyclic and/or rearrangement products.
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spelling pubmed-78848762021-02-24 Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride Lansbergen, Beatrice Meister, Catherine S McLeod, Michael C Beilstein J Org Chem Letter A novel reactivity of 1,1,1-trifluoroalkanones is reported, where the reaction with AlCl(3) results in the formation of 1,1-dichloro-1-alkenones. The reaction scope was found to be broad, with various chain lengths and aryl substituents tolerated. For substrates containing an electron-rich aromatic ring, further reactions take place, resulting in bicyclic and/or rearrangement products. Beilstein-Institut 2021-02-10 /pmc/articles/PMC7884876/ /pubmed/33633808 http://dx.doi.org/10.3762/bjoc.17.36 Text en Copyright © 2021, Lansbergen et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Letter
Lansbergen, Beatrice
Meister, Catherine S
McLeod, Michael C
Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride
title Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride
title_full Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride
title_fullStr Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride
title_full_unstemmed Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride
title_short Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride
title_sort unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7884876/
https://www.ncbi.nlm.nih.gov/pubmed/33633808
http://dx.doi.org/10.3762/bjoc.17.36
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