Add time:09/25/2019         Source:sciencedirect.com

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 (CH3)3SiCl with 1 gave the corresponding silylenolether (3), which did not yield cross condensation products with ketones. In the presence of TiCl4 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 ZnCl2. It is interesting to note that trimethylsiloxycyclohexene reacted with 1 in a Mukaiyama-aldol-condensation to the corresponding cross condensation product 13. Starting from (CF3)2CC(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 C2H5OH/H2O. A second double bond was introduced in an allylic position of the hexene ring by bromination and elimination with (C2H5)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.

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