peri-Naphthylenediamines. 33. Further studies of the reactions of 1,8-bis(dimethylamino)naphthalene with trifluoroacetic anhydride |
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Authors: | E Yu Romanova A F Pozharskii G S Borodkin |
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Institution: | (1) Rostov State University, 7 ul. Zorge, 344090 Rostov-on-Don, Russian Federation;(2) Institute of Physical and Organic Chemistry, 194/2 prosp. Stachki, 344090 Rostov-on-Don, Russian Federation |
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Abstract: | The reaction of 1,8-bis(dimethylamino)naphthalene (1) ( proton sponge ) with 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 naphtho1,8-c,d]pyran series, the double proton sponge (4), its di- (5) and tetrafluoroacetyl (6) derivatives, and compound 7. These results differ substantially from those obtained previously in the reactions performed in various solvents. Some conversions of compounds 4 and 7 were investigated. The 19F NMR spectra of the compounds synthesized are discussed. |
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Keywords: | 1 8-bis(dimethylamino)naphthalene proton sponge gif" alt="ldquo" align="MIDDLE" BORDER="0">proton sponge " target="_blank">gif" alt="rdquo" align="MIDDLE" BORDER="0"> trifluoroacetic anhydride electrophilic substitution 1H and 19F NMR spectra |
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