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Allylation of Orthoquinones Towards Annulated Polycyclic Aromatic Systems

1
Faculty of Chemistry, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland
2
Faculty of Chemistry, Nicolaus Copernicus University in Toruń, Gagarina 7, 87-100 Toruń, Poland
*
Author to whom correspondence should be addressed.
Present address: Centre of New Technologies, University of Warsaw, Banacha 2c, 02 097 Warsaw, Poland.
Molecules 2018, 23(8), 2043; https://doi.org/10.3390/molecules23082043
Received: 10 July 2018 / Revised: 12 August 2018 / Accepted: 13 August 2018 / Published: 15 August 2018
(This article belongs to the Section Organic Chemistry)
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Abstract

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. View Full-Text
Keywords: allylation; polycyclic aromatic compounds (PACs); orthoquinones; pinacol rearrangement; Wagner-Meerwein rearrangement; metathesis; tris(pentafluorophenyl)borane allylation; polycyclic aromatic compounds (PACs); orthoquinones; pinacol rearrangement; Wagner-Meerwein rearrangement; metathesis; tris(pentafluorophenyl)borane
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kędziorek, M.; Dobrzańska, L. Allylation of Orthoquinones Towards Annulated Polycyclic Aromatic Systems. Molecules 2018, 23, 2043.

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