The preferred conformation of erythro- and threo-1,2-difluorocyclododecanes

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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 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.

Original languageEnglish
Pages (from-to)1271-1278
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume8
DOIs
Publication statusPublished - 10 Aug 2012

Keywords

  • Alicyclic chemistry
  • Conformational analysis
  • Cyclododecane
  • 19F NMR
  • Organo-fluorine chemistry
  • Transannular interactions

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