Issue 40, 2014
From the journal:

Chemical Communications

Gold(i) mediated rearrangement of [7]-helicene to give a benzo[cd]pyrenium cation embedded in a chiral framework†

Raphael J. F. Berger,a   Matthew J. Fuchter,*b   Ingo Krossing,c   Henry S. Rzepa,b   Julia Schaeferc  and  Harald Schererc  

* Corresponding authors

a Chemistry of Materials, Hellbrunnerstr. 34, Paris Lodron-Universität Salzburg, A-5020 Salzburg, Austria

b Department of Chemistry, Imperial College London, London SW7 2AZ, UK
E-mail: m.fuchter@imperial.ac.uk
Tel: +44 (0)2075945815

c Institute for Inorganic and Analytical Chemistry, Freiburger Materialforschungszentrum FMF and Freiburg Institute for Advanced Studies (FRIAS), Albert–Ludwigs–Universität Freiburg, Albertstr. 21, 79104 Freiburg, Germany

Abstract

The facile gold-mediated skeletal rearrangement of [7]-helicene into a cationic polyaromatic hydrocarbon is described. We report in-depth studies on the structure and aromaticity of this novel stable cation and propose a mechanism for its formation.

Graphical abstract: Gold(i) mediated rearrangement of [7]-helicene to give a benzo[cd]pyrenium cation embedded in a chiral framework

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Article information

DOI
https://doi.org/10.1039/C3CC46986G
Article type
Communication
Submitted
12 Leo 2013
Accepted
28 Mph 2013
First published
30 Mph 2013

Chem. Commun., 2014,50, 5251-5253

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Gold(I) mediated rearrangement of [7]-helicene to give a benzo[cd]pyrenium cation embedded in a chiral framework

R. J. F. Berger, M. J. Fuchter, I. Krossing, H. S. Rzepa, J. Schaefer and H. Scherer, Chem. Commun., 2014, 50, 5251 DOI: 10.1039/C3CC46986G

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