J.J. Danon
Triply Threaded [4]Rotaxanes
Danon, J.J.; Leigh, D.A.; McGonigal, P.R.; Ward, J.W.; Wu, J.
Abstract
[4]Rotaxanes featuring three axles threaded through a single ring have been prepared through active metal template synthesis. Nickel-catalyzed sp3-sp3 homocouplings of alkyl bromide ‘half threads’ through 37- and 38-membered 2,2':6',2"-terpyridyl macrocycles generates triply-threaded [4]rotaxanes in up to 11 % yield. An analogous 39-membered macrocycle produced no rotaxane products under similar conditions. The constitutions of the [4]rotaxanes were determined by NMR spectroscopy and mass spectrometry. Doubly-threaded [3]rotaxanes were also obtained from the reactions but no [2]rotaxanes were isolated, suggesting that upon demetallation the axle of a singly-threaded rotaxane can slip through a macrocycle that is sufficiently large to accommodate three threads.
Journal Article Type | Article |
---|---|
Acceptance Date | Aug 29, 2016 |
Online Publication Date | Aug 29, 2016 |
Publication Date | Sep 28, 2016 |
Deposit Date | Sep 4, 2016 |
Publicly Available Date | Sep 5, 2016 |
Journal | Journal of the American Chemical Society |
Print ISSN | 0002-7863 |
Electronic ISSN | 1520-5126 |
Publisher | American Chemical Society |
Peer Reviewed | Peer Reviewed |
Volume | 138 |
Issue | 38 |
Pages | 12643-12647 |
DOI | https://doi.org/10.1021/jacs.6b07733 |
Public URL | https://durham-repository.worktribe.com/output/1375524 |
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Copyright Statement
ACS AuthorChoice - This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
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