AI Article Synopsis
- The study focuses on the synthesis of anilinocyclophanes using naturally occurring terpenes like citronellol, geraniol, and farnesol.
- The resulting compounds show significant ring strain, reaching up to 31 kcal/mol, which affects their molecular structure and chirality.
- The research reveals unexpected results, such as the production of isomerized neraniline, illustrating how ring strain impacts the stability and reactivity of these cyclophanes.
Article 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 -cyclophanes.
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| http://dx.doi.org/10.1021/jacs.4c06308 | DOI Listing |
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