Chemistry of organo halogenic molecules. Part 100. Comparative behaviour of xenon diflouride and caesium fluoroxysulphate in the fluorination of enol acetates and ketones

Abstract

Xenon difluoride and caesium fluoroxysulphate reacted in methylene chloride or acetonitrile with various enol acetates, diketones, and ketones, yielding mainly α-fluoro ketones, the course of the reaction depending on the reagent and the structure of the organic molecule. Enol acetates from cycloakanones were converted with caesium fluoroxysulphate to α-fluorocycloalkanones in high yield. Xenon difluoride and caesium fluoroxysulphate converted enol acetates of benzocycloalkanones-1 to α-fluorobenzocycloalkanones, while the reactivity of enol acetates of benzocycloalkanones-2 depended on the reagent used. 1,3-Diphenyl- propane-1,3-dione and its enol acetate were converted with XeF 2 and CsSO 4F to mono and difluoro substituted products, the course of the reaction being dependent on the reagent. Xenon difluoride converted 1-indanone to rearranged 2,2-difluorochromane, while caesium fluoroxysulphate reacted to 1-fluoro-2-indanone with 2-indanone.