Allylation of Orthoquinones Towards Annulated Polycyclic Aromatic Systems

Promising results of an efficient and convenient strategy for the annulation of polycyclic aromatic compounds (PACs), employing orthoquinones as starting material and comprising allylation, pinacol rearrangement, ring-closing metathesis (RCM), and one-pot reduction followed by Wagner-Meerwein rearra...

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Autores principales: Kędziorek, Mariusz, Dobrzańska, Liliana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222356/
https://www.ncbi.nlm.nih.gov/pubmed/30111725
http://dx.doi.org/10.3390/molecules23082043
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author Kędziorek, Mariusz
Dobrzańska, Liliana
author_facet Kędziorek, Mariusz
Dobrzańska, Liliana
author_sort Kędziorek, Mariusz
collection PubMed
description Promising results of an efficient and convenient strategy for the annulation of polycyclic aromatic compounds (PACs), employing orthoquinones as starting material and comprising allylation, pinacol rearrangement, ring-closing metathesis (RCM), and one-pot reduction followed by Wagner-Meerwein rearrangement, are presented. The strategy involves introducing triallylborane prepared in situ in the allylation step. Moreover, a novel expedient method for the preparation of 9,10-diallylphenanthrene was introduced.
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spelling pubmed-62223562018-11-13 Allylation of Orthoquinones Towards Annulated Polycyclic Aromatic Systems Kędziorek, Mariusz Dobrzańska, Liliana Molecules Communication Promising results of an efficient and convenient strategy for the annulation of polycyclic aromatic compounds (PACs), employing orthoquinones as starting material and comprising allylation, pinacol rearrangement, ring-closing metathesis (RCM), and one-pot reduction followed by Wagner-Meerwein rearrangement, are presented. The strategy involves introducing triallylborane prepared in situ in the allylation step. Moreover, a novel expedient method for the preparation of 9,10-diallylphenanthrene was introduced. MDPI 2018-08-15 /pmc/articles/PMC6222356/ /pubmed/30111725 http://dx.doi.org/10.3390/molecules23082043 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Kędziorek, Mariusz
Dobrzańska, Liliana
Allylation of Orthoquinones Towards Annulated Polycyclic Aromatic Systems
title Allylation of Orthoquinones Towards Annulated Polycyclic Aromatic Systems
title_full Allylation of Orthoquinones Towards Annulated Polycyclic Aromatic Systems
title_fullStr Allylation of Orthoquinones Towards Annulated Polycyclic Aromatic Systems
title_full_unstemmed Allylation of Orthoquinones Towards Annulated Polycyclic Aromatic Systems
title_short Allylation of Orthoquinones Towards Annulated Polycyclic Aromatic Systems
title_sort allylation of orthoquinones towards annulated polycyclic aromatic systems
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222356/
https://www.ncbi.nlm.nih.gov/pubmed/30111725
http://dx.doi.org/10.3390/molecules23082043
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AT dobrzanskaliliana allylationoforthoquinonestowardsannulatedpolycyclicaromaticsystems

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