Macrocyclization and molecular interlocking via Mitsunobu alkylation:: Highlighting the role of C-H•••O interactions in templating

[GRAPHICS] A series of diimide-based macrocycles have been prepared using Mitsunobu mediated alkylation as the macrocyclization step. These macrocycles could not be incorporated into [2]catenanes using previously established building blocks and coupling methodology. However, when one of the macrocycle syntheses was conducted in the presence of a dinaphtho crown ether, catenane formation was achieved. This result is discussed in terms of the ability of the components to establish intermolecular C-H ... O hydrogen-bonding contacts.