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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 | 28460462 | |
dc.identifier | 97bdce79-a547-426b-8a39-0d7e420a9ec0 | |
dc.identifier | 000307439600001 | |
dc.identifier | 84865268560 | |
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 | 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.format.extent | 1964252 | |
dc.language.iso | eng | |
dc.relation.ispartof | Beilstein Journal of Organic Chemistry | 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.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 | 10.3762/bjoc.8.143 | |
dc.description.status | Peer reviewed | en |
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