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Macrocyclization and Molecular Interlocking via Mitsunobu Alkylation:  Highlighting the Role of C−H···O Interactions in Templating

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journal contribution
posted on 2000-01-26, 00:00 authored by Jimmi G. Hansen, Neil Feeder, Darren G. Hamilton, Maxwell J. Gunter, Jan Becher, Jeremy K. M. Sanders
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.