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WangBeilsteinJnlOrgchem2012_8PreferredConformation.pdf1.92 MBAdobe PDFView/Open
Title: The preferred conformation of erythro- and threo-1,2-difluorocyclododecanes
Authors: Wang, Yi
Kirsch, Peer
Lebl, Tomas
Slawin, Alexandra M. Z.
O'Hagan, David
Keywords: Alicyclic chemistry
Conformational analysis
Organo-fluorine chemistry
Transannular interactions
QD Chemistry
Issue Date: 10-Aug-2012
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 . , 10.3762/bjoc.8.143
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.
Version: Publisher PDF
Status: Peer reviewed
ISSN: 1860-5397
Type: Journal article
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: (
Appears in Collections:Biomedical Sciences Research Complex (BSRC) Research
Chemistry Research
University of St Andrews Research

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