Macrocyclization and molecular interlocking via Mitsunobu alkylation: highlighting the role of C-H...O interactions in templating
[reaction: see text] 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.
Hansen
JG
University Chemical Laboratory, University of Cambridge, UK.
Feeder
N
Hamilton
DG
Gunter
MJ
Becher
J
Sanders
JK