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Use of Cleavable Coordinating Rings as Protective Groups in the Synthesis of a Rotaxane with an Axis that Incorporates More Chelating Groups Than Threaded Macrocycles

Abstract : A new methodology allowing preparation of a linear “unsaturated” [3]rotaxane consisting of an axis incorporating more coordination sites than threaded rings was developed. It was based on the preliminary synthesis of a “saturated” [5]rotaxane consisting of a four‐chelating site axis threaded through four macrocyclic components, two of them being cleavable rings incorporating a lactone function and the two others being “secure” non‐cleavable rings. The stoppering reaction was based on click chemistry. Subsequently, cleavage and removal of the two lactone‐containing macrocycles from the [5]rotaxane in basic medium afforded the desired “unsaturated” [3]rotaxane in quantitative yield.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02548575
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Submitted on : Monday, April 20, 2020 - 5:33:12 PM
Last modification on : Tuesday, April 21, 2020 - 2:03:30 AM

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Antoine Joosten, Yann Trolez, Valérie Heitz, Jean-Pierre Sauvage. Use of Cleavable Coordinating Rings as Protective Groups in the Synthesis of a Rotaxane with an Axis that Incorporates More Chelating Groups Than Threaded Macrocycles. Chemistry - A European Journal, Wiley-VCH Verlag, 2013, 19 (38), pp.12815-12823. ⟨10.1002/chem.201301717⟩. ⟨hal-02548575⟩

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