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Updated: Jun 21, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Enolization regioselectivity involving stereoisomeric 4a-methyl-5-methoxyperhydrobenzo[7]annulen-2-ones
Xiaozhao Wang1, Sean C Butler, Judith C Gallucci
1Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA.
Abstract:
Efficient synthetic routes to the four isomers 17b-20b of the title ketone are described. Entry begins from the Wieland-Miescher homologue 3 whose pair of carbonyl groups are amenable to regiochemical manipulation. The compositions of the reaction mixtures generated under kinetic or thermodynamic control were defined by (1)H NMR analysis subsequent to chromatographic purification. The regiochemical trends are correlated with B3LYP/6-31G* calculations, the results of which conform to the preferred introduction of a 1,2- or 2,3-double bond.
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