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Updated: Jun 17, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Terpenoid Cyclophanes with Planar Chirality
Alina Trofimova1, Matthew Diamandas1, Chelsey Brien1
1Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto M5S 3H6, Canada.
Abstract:
The strain-induced chirality of cyclophanes has attracted interest within the synthetic community. Herein, we report the synthesis of anilinocyclophanes derived from naturally occurring terpenes, such as citronellol, geraniol, and farnesol. The resulting cyclic oligoprenyl molecules exhibit considerable ring strain (up to 31 kcal/mol), as evident from their bent aniline planes, and possess chirality across the planes of an aryl ring and double bonds. Unexpected outcomes, such as the formation of isomerized neraniline, highlight the influence of ring strain on the stability and reactivity of terpenoid para-cyclophanes.
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