期刊
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
卷 191, 期 3, 页码 527-534出版社
TAYLOR & FRANCIS LTD
DOI: 10.1080/10426507.2015.1094659
关键词
ylides; Carbenes; zwitterion; ylenes; fluoroolefin; pentafluorosiliconate
资金
- University of Alabama [RG14648]
- DuPont
- Feodor-Lynen Fellowship from the Alexander von Humboldt Foundation
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 nonpolarized 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.
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