✍ Scribed by P.L. Coe; B.T. Croll; C.R. Patrick
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AWrut-1.2,3.4-TetraHuoroanthraquinone has been synthesized and some of its reactions studied Further reactions of tetrafluorophthalic acid and its derivatives arr reported.
tctraffuorophthalic acid and some of its reactions have been reported. This paper describes further reactions of the phthalic acid and its derivatives.
Reaction of tetrafluorophthalic acid or its anhydride with benzene under Friedel Crafts conditions" gave o-bcnzoyl-tetraduorobcnzoic acid, in good yield, which on heating with sulphuric acid gave 1,2,3,4_tetrafluoroanthraquinone, as pale yellow crystals in reasonable yield. The quinone showed a remarkable similarity to the corresponding hydrocarbon in its U.V. spectrum.
Attempts to reduce the quinonc under a variety of conditions either to the 9.10dihydro-or to 1.2.3.4tetrafluoroanthracene were unsuccessful. The products obtained were all rapidly rc-oxidizd to the quinone.
Nucleophilic displacement reactions have been carried out on the quinone; for example reaction with sodium methoxide gave a mixture of products, one constituting about 95% of the whole. The latter was indicated by elemental analysis to be a mcthoxy-trifluoroanthraquinonc, the PMR. spectrum of which was consistent with 2-methoxyl-1,3+trifluoroanthraquinone.
This result suggests that 1.2.3.4 tetratIuoroanthraquinone is most susceptible to nucleophilic attack in the 2-position, similar to the cases of 1,2,3,4_tetraIluoro-' and octafluoronaphthalene,* and in accord with the recently published rationlisation of nucleophilic substitution in polyfluoroaromatic compounds.8 Tetrafluorophthalic acid or its ethyl ester were readily reduced with LAH to 1,2-bis(hydroxymethyl) tetrafluorobcnzene.
Bromination of the latter with hydrogen bromide gave the highly lachrymatory 3,4,5,6-CetratIuoro-o-xylylene dibromide. The hydrocarbon analogue of the latter has been used as starting material in the synthesis of bcnzocyclobutcnc.' and it was of interest to establish whether the fluorine atoms in our compound would be used to stabilize bcnzocyclobutcne systems.
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