Chemistry of Haloperfluoro Compounds. Reactions of Metal F-Alkoxides and Metal F-Acetates with F-2-Butyne.
Final rept. 1 Jan 71-31 Dec 75,
CORNELL UNIV ITHACA N Y DEPT OF CHEMISTRY
Pagination or Media Count:
Methods were developed for the preparation of a variety of new carbon-oxygen-fluorine containing compounds utilizing as starting reagents metal F-alkoxides, derived from the corresponding carbonyl compound and metal fluorides, or F-acetates, and F-2-butyne. E-2-Bromo-3-F-alkoxy-F-2-butenes were prepared by the addition of silver F-alkoxides to F-2-butyne in the presence of the bromine transfer reagent 1,2-dibromotetrachlorethane. F-1,2,4,4,6,6-Hexamethyl-3, 5-dioxacyclohexene, IX, and F-3,4-dimethyl-3-penten-2-one, X, were formed by the reaction of E-F-1-methyl-propenylsilver with F-propanone and by the reaction of F-propanone with F-2-butyne in the presence of cesium fluoride. Compound X was also prepared from F-propanone and F-2-butyne in the presence of silver F-acetate. Compound X readily underwent photochemical cyclization to give F-1,2,4,4-tetramethyl-3-oxacyclobutene, XI. The thermal reactions of IX and XI and the reactions of IX, X and XI with cesium fluoride were investigated. The order of thermodynamic stability was IXXXI. Reaction of silver F-acetate with F-2-butyne in the presence of 1,2-di-bromotetrachloroethane gave E,Z-2-bromo-3-F-acetoxy-F-2-butene, XIII. Author
- Organic Chemistry