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A Concise Synthesis Of A Methyl Ester 2-Resorcinarene: A Chair-Conformation Macrocycle, Michael R. Reynolds, Fraser S. Pick, John J. Hayward, John F. Trant

Chemistry and Biochemistry Publications

Anions are important hydrogen bond acceptors in a range of biological, chemical, environ-mental and medical molecular recognition processes. These interactions have been exploited for the design and synthesis of ditopic resorcinarenes as the hydrogen bond strength can be tuned through the modification of the substituent at the 2-position. However, many potentially useful compounds, especially those incorporating electron-withdrawing functionalities, have not been prepared due to the challenge of their synthesis: their incorporation slows resorcinarene formation that is accessed by electrophilic aromatic substitution. As part of our broader campaign to employ resorcinarenes as selective recognition elements, we need access to these specialized …