Reaction of 5,5,5-trifluoro-4-(trifluoromethyl)penta-3-en-2-one ( 1) with p-toluene-sulfonylhydrazines under basic conditions provided anti-Michael addition products. Acid-catalyzed reactions yielded the expected hydrazones. In the absence of solvent the reaction of (CH 3) 3SiCl with 1 gave the corresponding silylenolether ( 3), which did not yield cross condensation products with ketones. In the presence of TiCl 4 silylenolether ( 3) reacted at −78°C to give the corresponding nonadienone ( 11). Analogously at 20°C condensation with water elimination gave the pyran system ( 12). The yields of 11 and 12 were increased by adding ZnCl 2. It is interesting to note that trimethylsiloxycyclohexene reacted with 1 in a Mukaiyama-aldol-condensation to the corresponding cross condensation product 13. Starting from (CF 3) 2CC(CN) 2 and a mixture of ( E/ Z)-1,3-pentadiene the expected cyclohexene was formed. One of the two CN-groups was removed with NaOH in C 2H 5OH/H 2O. A second double bond was introduced in an allylic position of the hexene ring by bromination and elimination with (C 2H 5) 3N to yield the diene. Reduction with DIBAlH provided the aldehyde 7,7,7,8,8,8-hexafluorosafranal. Hydrogenation of the C3–C4 double bond in the presence of palladium on a charcoal catalyst led to 7,7,7,8,8,8-hexafluoro-β-cyclocitral. X-ray structures of selected compounds are provided.