Rearrangements of Cycloalkenyl Aryl Ethers

Rearrangement reactions of cycloalkenyl phenol and naphthyl ethers and the acid-catalyzed cyclization of the resulting product were investigated. Claisen rearrangement afforded 2-substituted phenol and naphthol derivatives. Combined Claisen and Cope rearrangement resulted in the formation of 4-subst...

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Autores principales: Törincsi, Mercedesz, Nagy, Melinda, Bihari, Tamás, Stirling, András, Kolonits, Pál, Novak, Lajos
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273085/
https://www.ncbi.nlm.nih.gov/pubmed/27104504
http://dx.doi.org/10.3390/molecules21040503
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author Törincsi, Mercedesz
Nagy, Melinda
Bihari, Tamás
Stirling, András
Kolonits, Pál
Novak, Lajos
author_facet Törincsi, Mercedesz
Nagy, Melinda
Bihari, Tamás
Stirling, András
Kolonits, Pál
Novak, Lajos
author_sort Törincsi, Mercedesz
collection PubMed
description Rearrangement reactions of cycloalkenyl phenol and naphthyl ethers and the acid-catalyzed cyclization of the resulting product were investigated. Claisen rearrangement afforded 2-substituted phenol and naphthol derivatives. Combined Claisen and Cope rearrangement resulted in the formation of 4-substituted phenol and naphthol derivatives. In the case of cycloocthylphenyl ether the consecutive Claisen and Cope rearrangements were followed by an alkyl migration. The mechanism of this novel rearrangement reaction is also discussed.
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spelling pubmed-62730852018-12-28 Rearrangements of Cycloalkenyl Aryl Ethers Törincsi, Mercedesz Nagy, Melinda Bihari, Tamás Stirling, András Kolonits, Pál Novak, Lajos Molecules Article Rearrangement reactions of cycloalkenyl phenol and naphthyl ethers and the acid-catalyzed cyclization of the resulting product were investigated. Claisen rearrangement afforded 2-substituted phenol and naphthol derivatives. Combined Claisen and Cope rearrangement resulted in the formation of 4-substituted phenol and naphthol derivatives. In the case of cycloocthylphenyl ether the consecutive Claisen and Cope rearrangements were followed by an alkyl migration. The mechanism of this novel rearrangement reaction is also discussed. MDPI 2016-04-19 /pmc/articles/PMC6273085/ /pubmed/27104504 http://dx.doi.org/10.3390/molecules21040503 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Törincsi, Mercedesz
Nagy, Melinda
Bihari, Tamás
Stirling, András
Kolonits, Pál
Novak, Lajos
Rearrangements of Cycloalkenyl Aryl Ethers
title Rearrangements of Cycloalkenyl Aryl Ethers
title_full Rearrangements of Cycloalkenyl Aryl Ethers
title_fullStr Rearrangements of Cycloalkenyl Aryl Ethers
title_full_unstemmed Rearrangements of Cycloalkenyl Aryl Ethers
title_short Rearrangements of Cycloalkenyl Aryl Ethers
title_sort rearrangements of cycloalkenyl aryl ethers
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273085/
https://www.ncbi.nlm.nih.gov/pubmed/27104504
http://dx.doi.org/10.3390/molecules21040503
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