Fluorination of terpenoid carbonyl compounds used in perfumery

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Reformatsky reaction of trifluoroacetaldehyde with lower bromoesters gave their corresponding adducts. The reaction of trifluoroacetaldehyde with methyl 2-(bromomethyl)acrylate gave gamma-trifluoromethyl-alpha-methylene-gamma-butyrolactone. Reformatsky reaction of terpenic aldehydes with difluoromonobromo acetate gave their corresponding adducts. The reaction of citronellal with difluoromonobromo acetate gave ethyl 2,2-difluoro-5,9-dimethyl-3-hydroxy-8-decenoate. Swern oxidation of these hydroxyesters gave their corresponding alpha, alpha-difluoro-beta-ketoesters.The reaction of trifluoromethyltrimethylsilane with a variety of terpenoid carbonyl compounds and other carbonyl compounds used in perfumery gave the corresponding trifluoromethylated derivatives. Pentafluoroethylated compounds were similarlly obtained from the reaction of pentafluoroethyltrimethylsilane with various substrate.(-)-2-Trifluoro-1-furyl ethanol has been obtained with high optical purity by enzymatic hydrolysis of 2-trifluoro-1-furyl ethyl acetate.We had expected that trifluoromethylated and pentafluoroethylated compounds derived from terpenoid compounds would have biological activity. However, our biological tests showed no antimicrobial activity agatint Gram positive and Gram negative bacteria, mycelial fungi and yeasts.