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

ISSN
1523-7060
Date Issued
2015-09-04
Author(s)
Vliegenthart, Annette B.
Welling, Frank A. L.
Roemelt, Michael
Klein Gebbink, Robertus J. M.
DOI
10.1021/acs.orglett.5b01931
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.