J. Xiang et al., STEREOSPECIFIC ALKENYLATION OF C-H BONDS VIA REACTION WITH BETA-HETEROATOM-FUNCTIONALIZED TRISUBSTITUTED VINYL TRIFLONES, Journal of the American Chemical Society, 119(18), 1997, pp. 4123-4129
Aryl and alkyl beta-heteroatom-trisubstituted vinyl triflones react wi
th THF and cyclohexane to undergo trifluoromethyl radical-mediated C-H
functionalization reactions to afford E and Z beta-heteroatom-trisubs
tituted olefins. Most reactions proceed with both high yield and high
stereospecificity (retention of configuration). beta-Substituents whic
h have been employed in this study are iodine, bromine, fluorine, benz
oate, ethylcarbonate, and phthalimide. beta-Substituents bearing power
ful electron-releasing groups such as alkoxy or amino render the vinyl
triflone unreactive.