Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups

Friedel–Crafts reactions of isopropyl-substituted benzenes with phthalic anhydride in the presence of aluminium trichloride, followed by cyclization of the products with strong sulfuric acid give, as expected, anthraquinones. The syntheses, however, often afford more than one anthraquinone. In some...

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Detalles Bibliográficos
Autores principales: Chakiri, Abdel B., Hodge, Philip
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society Publishing 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5579107/
https://www.ncbi.nlm.nih.gov/pubmed/28878991
http://dx.doi.org/10.1098/rsos.170451
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author Chakiri, Abdel B.
Hodge, Philip
author_facet Chakiri, Abdel B.
Hodge, Philip
author_sort Chakiri, Abdel B.
collection PubMed
description Friedel–Crafts reactions of isopropyl-substituted benzenes with phthalic anhydride in the presence of aluminium trichloride, followed by cyclization of the products with strong sulfuric acid give, as expected, anthraquinones. The syntheses, however, often afford more than one anthraquinone. In some cases the isopropyl groups migrate cleanly to other ring positions; in other cases they are lost.
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spelling pubmed-55791072017-09-06 Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups Chakiri, Abdel B. Hodge, Philip R Soc Open Sci Chemistry Friedel–Crafts reactions of isopropyl-substituted benzenes with phthalic anhydride in the presence of aluminium trichloride, followed by cyclization of the products with strong sulfuric acid give, as expected, anthraquinones. The syntheses, however, often afford more than one anthraquinone. In some cases the isopropyl groups migrate cleanly to other ring positions; in other cases they are lost. The Royal Society Publishing 2017-08-23 /pmc/articles/PMC5579107/ /pubmed/28878991 http://dx.doi.org/10.1098/rsos.170451 Text en © 2017 The Authors. http://creativecommons.org/licenses/by/4.0/ Published by the Royal Society under the terms of the Creative Commons Attribution License http://creativecommons.org/licenses/by/4.0/, which permits unrestricted use, provided the original author and source are credited.
spellingShingle Chemistry
Chakiri, Abdel B.
Hodge, Philip
Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups
title Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups
title_full Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups
title_fullStr Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups
title_full_unstemmed Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups
title_short Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups
title_sort synthesis of isopropyl-substituted anthraquinones via friedel–crafts acylations: migration of isopropyl groups
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5579107/
https://www.ncbi.nlm.nih.gov/pubmed/28878991
http://dx.doi.org/10.1098/rsos.170451
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