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One-pot synthesis and AFM imaging of a triangular aramide macrocycle

Storz, Christof ; Badoux, Michael ; Hauke, Christopher M. ; Šolomek, Tomáš ; Kühnle, Angelika ; Bally, Thomas ; Kilbinger, Andreas F. M.

In: Journal of the American Chemical Society, 2014, vol. 136, no. 37, p. 12832–12835

Macrocyclizations in exceptionally good yields were observed during the self-condensation of N-benzylated phenyl p-aminobenzoates in the presence of LiHMDS to yield three-membered cyclic aramides that adopt a triangular shape. An ortho-alkyloxy side chain on the N-benzyl protecting group is necessary for the macrocyclization to occur. Linear polymers are formed exclusively in the absence of this...