Influence of the difluoromethylene group (CF<sub>2</sub>) on the conformation and properties of selected organic compounds

O'Hagan, David; Wang, Yi; Skibinski, Maciej; Slawin, Alexandra M. Z.

doi:10.1351/PAC-CON-11-09-26

Pure Appl. Chem., 2012, Vol. 84, No. 7, pp. 1587-1595

http://dx.doi.org/10.1351/PAC-CON-11-09-26

Published online 2012-04-07

Influence of the difluoromethylene group (CF₂) on the conformation and properties of selected organic compounds

David O'Hagan*, Yi Wang, Maciej Skibinski and Alexandra M. Z. Slawin

EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK

Abstract: The CF₂ group has found applications as a substituent in all classes of organic chemical products from medicinal products to materials, although it is less frequently encountered than the C–F and CF₃ substituents. In this review, the geometric influence of placing two fluorine atoms on carbon is considered and in particular, deviations from tetrahedral geometry are noted. The incorporation of the CF₂ group into CF₂ phosphonates as phosphate mimics is reviewed and the geometric and steric influences of the CF₂ group are considered when the substituent is placed within aliphatic chains and aliphatic ring (cyclododecane) systems.