1. Reactions of imidazol(in)-2-ylidenes with electron deficient fluoroolefins
- Author
-
Arduengo, Anthony J., Calabrese, Joseph C., H. V. Rasika Dias, Davidson, Fredric, Goerlich, Jens R., Jockisch, Alexander, Kline, Michael, Marshall, William J., and Runyon, Jason W.
- Abstract
1,3-Bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene forms stable 1:1 adducts with tetrafluoroethylene (2), hexafluorocyclobutene (3) and octafluorocyclopentene (4). Adduct 2 shows properties typical for non-polarized olefins, as indicated by NMR spectroscopy and X-ray crystallography. By contrast, adducts 3 and 4 are best described as ylides with a significant charge separation between the imidazoline ring and the perfluorocycloalkyl unit. Similarly, 1,3-di-1-adamantylimidazol-2-ylidene reacts with tetrakis(trifluoromethyl)allene to form a polarized trimethylenemethane derivative, and bis(trifluoromethyl)ketene to form an imidazolium enolate zwitterion. The synthesis and characterization of a number of fluorinated methyleneimidazolines are described herein.
- Published
- 2016
- Full Text
- View/download PDF