Issue 65, 2012
From the journal:

Chemical Communications

An experimental estimate of the relative aromaticity of the cyclooctatetraene dianion by fusion to dimethyldihydropyrene†‡

Reginald H. Mitchell,*a   Pengrong Zhang,a   David J. Berga  and  Richard Vaughan Williamsb  

* Corresponding authors

a Department of Chemistry, University of Victoria, P.O. Box 3065, Victoria, BC, Canada
E-mail: regmitch@uvic.ca
Fax: 1250 721 7147
Tel: 1250 721 7152

b Department of Chemistry, University of Idaho, P.O. Box 442343, Moscow, United States
E-mail: williams@uidaho.edu
Fax: 1208 885 6173
Tel: 1208 885 6775

Abstract

The synthesis of the cyclooctatetraene dianion (COT2−) fused at the [e]-position of trans-10b,10c-dimethyl-10b,10c-dihydropyrene (DHP) is described, and by comparison of 1H NMR properties and NICSAv to the analogous benzene fused DHP, the relative aromaticity of the dianion is found to be at least as great as that of benzene, and substantially larger than that of the cyclopentadienide anion.

Graphical abstract: An experimental estimate of the relative aromaticity of the cyclooctatetraene dianion by fusion to dimethyldihydropyrene

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

DOI
https://doi.org/10.1039/C2CC33518B
Article type
Communication
Submitted
15 May 2012
Accepted
26 Jun 2012
First published
10 Jul 2012

Chem. Commun., 2012,48, 8144-8146

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An experimental estimate of the relative aromaticity of the cyclooctatetraene dianion by fusion to dimethyldihydropyrene

R. H. Mitchell, P. Zhang, D. J. Berg and R. V. Williams, Chem. Commun., 2012, 48, 8144 DOI: 10.1039/C2CC33518B

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