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Synthesis and Characterization of a Brønsted Pair Functionalized Shape-Persistent Macrocycle

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Roemelt,  Michael
Research Group Roemelt, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Lehrstuhl für Theoretische Chemie, Ruhr-Universität Bochum;

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ol5b01931_si_001.pdf
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Citation

Vliegenthart, A. B., Welling, F. A. L., Roemelt, M., Klein Gebbink, R. J. M., & Otte, M. (2015). Synthesis and Characterization of a Brønsted Pair Functionalized Shape-Persistent Macrocycle. Organic Letters, 17(17), 4172-4175. doi:10.1021/acs.orglett.5b01931.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0029-6F99-F
Abstract
The first shape-persistent macrocycle 1 offering a Brønsted pair functionalized interior is described. Via postcyclization transformation, this heterosequenced compound can be obtained from its corresponding ester 2. The macrocycles differ dramatically in their characteristics such as solubility and appearance. Theoretical investigations suggest that those contrasts might originate from conformational changes due to the formation of a strong O–H–N hydrogen bond in 1.