peri-Naphthylenediamines 33. Further studies of the reactions of 1,8-bis(dimethylamino)naphthalene with trifluoroacetic anhydride

The reaction of 1,8 -bis(dimethylamino) naphthalene (1) ("proton sponge") w ith a large excess of trifluoroacetic anhydride in the absence of a solvent afforded a complex mixture of products among which were trans- (2) and cis -diols (3) of the naphtho[1,8-c,d]pyran series, the double "proton sponge" (4), its di- (5) and tetrafluoroacetyl (6) derivatives, and compound 7. The se results differ substantially from those obtained previously in the react ions performed in various solvents. Some conversions of compounds 4 and 7 w ere investigated. The F-19 NMR spectra of the compounds synthesized are dis cussed.