The reactivity of the enolate of the 4-carbethoxy-3-trifluoromethyl-cyclohex-2-enone (1) toward electrophiles has been studied and compared with that of the parent Hagemann's ester. Presence of the CF 3 group could allow the selective introduction of substituents at three different sites. With alkyl halides the C-2 alkylation is completely favored. High selectivity is directed to the C-4 site with ethyl chloroformate, and only O-silylation occurred with a silylated chloride.