Volume 92 Issue 29 | p. 29 | Concentrates
Issue Date: July 21, 2014

Caged Lithium Speeds Fullerene Cycloadditions

Encapsulated ion acts as a Lewis acid catalyst
Department: Science & Technology
News Channels: Organic SCENE, Materials SCENE, JACS In C&EN
Keywords: fullerene, buckyball, Diels-Alder, cycloaddition

To get more zip out of Diels-Alder reactions, chemists often employ a Lewis acid catalyst to starve the cycloaddition’s dienophile of electron density as it seeks out the electron-rich diene. One problem with this approach is that a heteroatom is needed in the dienophile to coordinate with certain Lewis acids, such as lithium ions. This coordination adds a steric component to the reaction, making it difficult to separate electronic and steric effects when teasing out . . .

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