R. D. Lousenberg, M. Shoichet
Oct 31, 1997
Citations
1
Influential Citations
12
Citations
Journal
Journal of Organic Chemistry
Abstract
Novel trifluorovinyl ethers (TFVEs, ROCFCF2), where R is an oligoether, were synthesized from the corresponding sodium alkoxide and hexafluoropropene oxide. The sodium alkoxide ring opened hexafluoropropene oxide at the more highly substituted carbon (C2) to give the 2-alkoxy-2,3,3,3-tetrafluoropropionic acid ester incorporating 2 equiv of the alcohol, ROCF(CF3)CO2R. Hydrolysis of the ester and reaction of the resulting sodium 2-alkoxy-2,3,3,3-tetrafluoropropionate with chlorotrimethylsilane gave the trimethylsilyl 2-alkoxy-2,3,3,3-tetrafluoropropionate, ROCF(CF3)CO2Si(CH3)3. Gas phase vacuum thermolysis of the trimethylsilyl ester at 140−150 °C gave the corresponding TFVEs in 55−63% yields. Thus, 1-[2-(ethoxyethoxy)ethoxy]-1,2,2-trifluoroethene and 1-[2-(2-tert-butoxyethoxy)ethoxy]-1,2,2-trifluoroethene were synthesized from 2-(2-ethoxyethoxy)ethanol and 2-(2-tert-butoxyethoxy)ethanol, respectively. Interestingly, thermolysis of sodium or potassium 2-alkoxy-2,3,3,3-tetrafluoropropionates resulted in negl...