Reactions of octafluoroacridone and related compounds

Abstract

A new route to polyfluoroacridones is described and the substitution reactions of octafluoroacridone with methoxide ion are discussed, the position of substitution being confirmed by alternative synthesis from an amino-methoxy-octafluorobenzophenone. From octafluoroacridone was prepared 9-chloro-octafluoroacridine, but not nonafluoroacridine, owing to its ready hydrolysis. Polyfluoroacridones give stable sodium salts, isolable in crystalline form.

Ready demethylation of methyl polyfluoroaryl ethers occurred with concentrated sulphuric acid when a carboxy-group or hydrogen atom was para to the methoxy-group; this is explained in terms of protonation of the para ring carbon atom.