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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
Author(s) -
Joosten Antoine,
Trolez Yann,
Heitz Valérie,
Sauvage JeanPierre
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301717
Subject(s) - rotaxane , chemistry , chelation , lactone , stereochemistry , cleavage (geology) , materials science , molecule , organic chemistry , supramolecular chemistry , fracture (geology) , composite material
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.