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The preferred conformation of erythro- and threo-1,2-difluorocyclododecanes
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dc.contributor.author | Wang, Yi | |
dc.contributor.author | Kirsch, Peer | |
dc.contributor.author | Lebl, Tomas | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.contributor.author | O'Hagan, David | |
dc.date.accessioned | 2012-11-22T15:31:03Z | |
dc.date.available | 2012-11-22T15:31:03Z | |
dc.date.issued | 2012-08-10 | |
dc.identifier.citation | Wang , Y , Kirsch , P , Lebl , T , Slawin , A M Z & O'Hagan , D 2012 , ' The preferred conformation of erythro- and threo-1,2-difluorocyclododecanes ' , Beilstein Journal of Organic Chemistry , vol. 8 , pp. 1271-1278 . https://doi.org/10.3762/bjoc.8.143 | en |
dc.identifier.issn | 1860-5397 | |
dc.identifier.other | PURE: 28460462 | |
dc.identifier.other | PURE UUID: 97bdce79-a547-426b-8a39-0d7e420a9ec0 | |
dc.identifier.other | WOS: 000307439600001 | |
dc.identifier.other | Scopus: 84865268560 | |
dc.identifier.other | ORCID: /0000-0002-0269-3221/work/48131713 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861725 | |
dc.identifier.other | ORCID: /0000-0002-0510-5552/work/68281256 | |
dc.identifier.uri | https://hdl.handle.net/10023/3261 | |
dc.description.abstract | Cyclododecane adopts a square-like structure with corner and edge CH2 groups. In this study erythro- and threo-1,2-difluorocyclododecanes were prepared to explore whether the two vicinal C-F bonds, with different relative configurations, preferably locate at corner/edge or edge/edge locations. Conformational analysis comparing the diastereoisomers was explored by using a combination of F-19{H-1} NMR spectroscopy, computational studies and, in the case of the threo isomer, X-ray structural analysis. In the lowest energy conformers for both diastereoisomers the vicinal C-F bonds are located corner/edge, rather than edge/edge. These structures avoid placing a C-F bond endo into the ring, and appear to benefit from C-CHF-C angle widening, which relaxes 1,4-H, H transannular interactions. | |
dc.format.extent | 8 | |
dc.language.iso | eng | |
dc.relation.ispartof | Beilstein Journal of Organic Chemistry | en |
dc.rights | © 2012 Wang et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc) | en |
dc.subject | Alicyclic chemistry | en |
dc.subject | Conformational analysis | en |
dc.subject | Cyclododecane | en |
dc.subject | 19F NMR | en |
dc.subject | Organo-fluorine chemistry | en |
dc.subject | Transannular interactions | en |
dc.subject | QD Chemistry | en |
dc.subject.lcc | QD | en |
dc.title | The preferred conformation of erythro- and threo-1,2-difluorocyclododecanes | en |
dc.type | Journal article | en |
dc.description.version | Publisher PDF | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.3762/bjoc.8.143 | |
dc.description.status | Peer reviewed | en |
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