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dc.contributor.authorWang, Yi
dc.contributor.authorKirsch, Peer
dc.contributor.authorLebl, Tomas
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorO'Hagan, David
dc.identifier.citationWang , 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 .
dc.identifier.otherPURE: 28460462
dc.identifier.otherPURE UUID: 97bdce79-a547-426b-8a39-0d7e420a9ec0
dc.identifier.otherWOS: 000307439600001
dc.identifier.otherScopus: 84865268560
dc.identifier.otherORCID: /0000-0002-0269-3221/work/48131713
dc.description.abstractCyclododecane 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.en
dc.relation.ispartofBeilstein Journal of Organic Chemistryen
dc.rights© 2012 Wang et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (, 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: (
dc.subjectAlicyclic chemistryen
dc.subjectConformational analysisen
dc.subject19F NMRen
dc.subjectOrgano-fluorine chemistryen
dc.subjectTransannular interactionsen
dc.subjectQD Chemistryen
dc.titleThe preferred conformation of erythro- and threo-1,2-difluorocyclododecanesen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.description.statusPeer revieweden

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