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 Author affiliations * 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. This article is part of the themed collection: Aromaticity You have access to this article Please wait while we load your content... Something went wrong. Try again?