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Org Lett. 2008 Nov 6;10(21):4835-8. doi: 10.1021/ol801919q. Epub 2008 Oct 11.

Supramolecular control of a fast and reversible Diels-Alder reaction.

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  • 1Dipartimento di Chimica and IMC-CNR, UniversitĂ  La Sapienza, P.le Aldo Moro 5, 00185 Roma, Italy. bernardo.masci@uniroma1.it


A new cyclophane featuring two opposite anthracene units linked in 9,10-positions has been synthesized thanks to the template effect of the Me4N(+) ion. It forms pseudorotaxane complexes with alkylviologen ions and undergoes a fast and reversible reaction with tetracyanoethylene. A quantitative analysis has been carried out of the formation of Diels-Alder adducts, whose distribution can be controlled by host-guest complexation. These findings open interesting perspectives in the field of Dynamic Covalent Chemistry.

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