An experimental estimate of the relative aromaticity of the cyclooctatetraene dianion by fusion to dimethyldihydropyrene.
The synthesis of the cyclooctatetraene dianion (COT(2-)) fused at the [e]-position of trans-10b,10c-dimethyl-10b,10c-dihydropyrene (DHP) is described, and by comparison of (1)H 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.
Department of Chemistry, University of Victoria, P.O. Box 3065, Victoria, BC V8V 3V6, Canada. regmitch@uvic.ca
Reginald H
RH
Mitchell
Pengrong
P
Zhang
David J
DJ
Berg
Richard Vaughan
RV
Williams