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

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.

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ol5b01931_si_001.pdf (Supplementary material), 8MB
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Vliegenthart, Annette B.1, Author
Welling, Frank A. L.1, Author
Roemelt, Michael2, 3, Author              
Klein Gebbink, Robertus J. M.1, Author
Otte, Matthias1, Author
Affiliations:
1Organic Chemistry & Catalysis, Debye Institute for Nanomaterials Science, Universiteit Utrecht, Universiteitsweg 99, 3584 CG Utrecht, The Netherlands, ou_persistent22              
2Research Group Roemelt, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_3018043              
3Lehrstuhl für Theoretische Chemie, Ruhr-Universität Bochum, ou_persistent22              

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 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.

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Language(s): eng - English
 Dates: 2015-07-062015-08-252015-09-04
 Publication Status: Published in print
 Pages: 4
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.orglett.5b01931
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Title: Organic Letters
  Other : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 17 (17) Sequence Number: - Start / End Page: 4172 - 4175 Identifier: ISSN: 1523-7060
CoNE: https://pure.mpg.de/cone/journals/resource/954925626338