REGIOSELECTIVE CARBON CARBON BOND FORMATION OF 2,2,2-TRIFLUOROETHYL SUBSTITUTED TERTIARY-AMINES INITIATED BY ELECTRON-TRANSFER TO PHOTOCHEMICALLY EXCITED ENONE

Photoadditions of N-(2,2,2-trifluoroethyl)amines to 3-phenylcyclohex-2-en-1-one occurred at the alpha-position to the trifluoromethyl group predominantly. The regioselectivity of this photoaddition reaction was comparable to that of anodic methoxylation of N-(2,2,2-trifluoroethyl)anilines; this reaction is the first example of direct carbon substitution at alpha to the trifluoromethyl group and this promotion effect was general for other electron-withdrawing groups.