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Issue 65, 2012
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An experimental estimate of the relative aromaticity of the cyclooctatetraene dianion by fusion to dimethyldihydropyrene

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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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Publication details

The article was received on 15 May 2012, accepted on 26 Jun 2012 and first published on 10 Jul 2012


Article type: Communication
DOI: 10.1039/C2CC33518B
Citation: 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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