Alicyclic Ring Structure: Conformational Influence of the CF2 Group in Cyclododecanes†
Maciej Skibinski
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/group
Search for more papers by this authorDr. Yi Wang
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/group
Search for more papers by this authorProf. Alexandra M. Z. Slawin
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/group
Search for more papers by this authorDr. Tomas Lebl
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/group
Search for more papers by this authorProf. Dr. Peer Kirsch
Merck KGaA, PM-A Emerging Technologies Germany, Frankfurter Str. 250, 64293 Darmstadt (Germany)
Search for more papers by this authorCorresponding Author
Prof. David O'Hagan
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/group
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/groupSearch for more papers by this authorMaciej Skibinski
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/group
Search for more papers by this authorDr. Yi Wang
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/group
Search for more papers by this authorProf. Alexandra M. Z. Slawin
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/group
Search for more papers by this authorDr. Tomas Lebl
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/group
Search for more papers by this authorProf. Dr. Peer Kirsch
Merck KGaA, PM-A Emerging Technologies Germany, Frankfurter Str. 250, 64293 Darmstadt (Germany)
Search for more papers by this authorCorresponding Author
Prof. David O'Hagan
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/group
EaStChem School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST (UK) http://chemistry.st-and.ac.uk/staff/doh/groupSearch for more papers by this authorD.O’H. thanks the ERC for an Advanced Investigator Grant to support this research.
Graphical Abstract
Man geht sich aus dem Weg: In fluorierten Cyclododecanen nimmt die CF2-Gruppe ausschließlich Eckpositionen ein (siehe Bild; blau C, grau H, grün F), wodurch transannulare 1,4-H,H-Wechselwirkungen infolge einer Aufweitung des C-CF2-C-Winkels relaxieren. Fehlgeordnete CF2-Gruppen verursachen hingegen eine signifikante Verzerrung der Ringstruktur. Der Einbau von CF2-Gruppen könnte daher als Designelement zur Einführung von Ordnung und Polarität in organische Kohlenwasserstoffstrukturen dienen.
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