Issue 65, 2012
From the journal:

Chemical Communications

Diels–Alder cycloaddition of acetylene gas to a polycyclic aromatic hydrocarbon bay region†

Eric H. Fort,a   Matthew S. Jeffreysa  and  Lawrence T. Scott*a  

* Corresponding authors

a Merkert Chemistry Center, Department of Chemistry, Boston College, Chestnut Hill, MA 02467-3860, USA
E-mail: lawrence.scott@bc.edu
Fax: 617-552-6454
Tel: 617-552-8024

Abstract

The direct conversion of a polycyclic aromatic hydrocarbon bay region to a new, unsubstituted benzene ring by Diels–Alder cycloaddition of acetylene gas is reported for the first time. At 140 °C in dimethylformamide, under 1.8 atm pressure of acetylene gas, 7,14-dimesitylbisanthene is slowly converted to 7,14-dimesitylbenzo[ghi]bisanthene (21% conversion in 48 h).

Graphical abstract: Diels–Alder cycloaddition of acetylene gas to a polycyclic aromatic hydrocarbon bay region

  • This article is part of the themed collection: Aromaticity
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Article information

DOI
https://doi.org/10.1039/C2CC33885H
Article type
Communication
Submitted
30 May 2012
Accepted
19 Jun 2012
First published
05 Jul 2012

Chem. Commun., 2012,48, 8102-8104

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Diels–Alder cycloaddition of acetylene gas to a polycyclic aromatic hydrocarbon bay region

E. H. Fort, M. S. Jeffreys and L. T. Scott, Chem. Commun., 2012, 48, 8102 DOI: 10.1039/C2CC33885H

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