T. Hanamoto, N. Morita, Keiko Shindo
Nov 1, 2003
Citations
0
Influential Citations
34
Citations
Journal
European Journal of Organic Chemistry
Abstract
(2,2,2-Trifluoroethyl)triphenylphosphonium trifluoromethanesulfonate (triflate) (1) was readily synthesized in high yield from triphenylphosphane and 2,2,2-trifluoroethyl triflate. The Wittig olefination of 1 with aromatic aldehydes bearing electron-withdrawing groups with CsF as a base in DMF proceeded cleanly, producing the corresponding 3,3,3-trifluoropropenylidene compounds in good yields. On the other hand, the hydrolysis of 1 in methanol containing sodium hydroxide gave (2,2-dimethoxyvinyl)triphenylphosphonium triflate (6a) in high yield instead of the corresponding (2,2,2-trifluoroethyl)diphenylphosphane oxide. Furthermore, reactions between 1 and secondary amines exclusively gave the novel (Z)-(2-amino-2-fluorovinyl)triphenylphosphonium triflates (10) in high yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)