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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Bibliographic Details
Published in:Molecules
Main Authors: Mariusz Kędziorek, Liliana Dobrzańska
Format: Article
Language:English
Published: MDPI AG 2018-08-01
Subjects:
allylation
polycyclic aromatic compounds (PACs)
orthoquinones
pinacol rearrangement
Wagner-Meerwein rearrangement
metathesis
tris(pentafluorophenyl)borane
Online Access:http://www.mdpi.com/1420-3049/23/8/2043
Description
Summary: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.
ISSN:1420-3049

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