Alicyclic Ring Structure: Conformational Influence of the CF2 Group in Cyclododecanes

Getting out of the way: In fluorinated cyclododecane structures the CF2 group locates only at corner positions (see picture). This relaxes 1,4‐H,H transannular interactions as a result of C‐CF2‐C angle widening. Misplaced CF2 groups lead to significant ring distortion. It follows that strategic inco...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2011-11, Vol.50 (45), p.10581-10584
Main Authors: Skibinski, Maciej, Wang, Yi, Slawin, Alexandra M. Z., Lebl, Tomas, Kirsch, Peer, O'Hagan, David
Format: Article
Language:English
Subjects:
conformational analysis
Crystallography, X-Ray
Hydrocarbons, Alicyclic - chemistry
Hydrocarbons, Fluorinated - chemistry
Magnetic Resonance Spectroscopy
Molecular Conformation
multivicinal fluorines
organic materials
organofluorine chemistry
Quantum Theory
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Summary:Getting out of the way: In fluorinated cyclododecane structures the CF2 group locates only at corner positions (see picture). This relaxes 1,4‐H,H transannular interactions as a result of C‐CF2‐C angle widening. Misplaced CF2 groups lead to significant ring distortion. It follows that strategic incorporation of CF2 groups has potential as a design feature to introduce order and polarity into organic hydrocarbon structures.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201105060