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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 19F{1H} 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.
Beilstein J. Org. Chem. 2012, 8, 1271–1278. doi:10.3762/bjoc.8.143
| Authors: | Yi Wang, Peer Kirsch, Tomas Lebl, Alexandra M. Z. Slawin and David O'Hagan | |
| Journal: | Beilstein Journal of Organic Chemistry | |
| Year: | 2012 | |
| DOI: | 10.3762/bjoc.8.143 | |
| Publication date: | 10-08-2012 |
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