ENE REACTION OF N-TOSYLHEXAFLUOROACETONE IMINE

As the extension of ene reaction of trifluoromethyl carbonyl compounds, ene reaction of N-tosylhexafluoroacetone imine (1) was examined. It reacted with terminal olefins to give α, α-bis(trifluoromethyl)amine derivatives in moderate to good yields. Inner olefins are much less reactive than terminal olefins, probably due to the steric effect of the substituents. Thus, cyclohexene and 2-octene gave the ene reaction products only in poor yields, and 1-phenylpropene did not give the ene reaction product at all but afforded an azetidine compound in a low yield.