Anthracene tetracarboxylate

Ozonolysis of 9,10-dibromo- (17a) and 9,10-dichloroanthracene (17b) was reported to occur partly by attack at the non-halogenated double bonds to yield the di- (18) and tetracarboxylic acids, 19, as well as by attack at the 9,10-positions to yield the dehalogenated product anthra-quinone, 22 (8). This dual attack might at first seem to be in contrast to what was said above about the relative rates of ozone attack at halo-genated and non-halogenated double bonds. However, this is not the case if one considers that (in analogy to the ozonolysis of the unsubstituted anthracene) the reaction at the 9,10-positions has to be formulated as an atom- rather than a bond attack. In accordance with such a rationalization, the authors (8) formulated the intermediates 20 and 21 as precursors for anthraquinone. 

Foster, R., Iball, J., Scrimgeour, S. N., and Williams, B. C. Crystal structure and nuclear magnetic resonance spectra of a 1 1 complex of benz[ a ]anthracene and pyromellitic dianhydride (benzene-1,2,4,5-tetracarboxylic dianhydride). J. Chem. Soc., Perkin Trans. II, 682-685 (1976). 

Takahashi et al. [105] reported a family of dendrimers with perylene tetracarboxylate cores and layers of 4, 8, 12, 16, or 24 anthracene imits at-... 

The high reactivity of benzynes as dienophiles in Diels-Alder reactions has also been observed in reactions with aromatic hydrocarbons, a class of compounds usually considered as inert as dienes. In a two-step synthesis of triptycene di- and tetracarboxylic acids, arynes generated in situ from anthranUic adds 158 cydized with anthracenes 159 affording di- or tetramethyltriptycenes 160 in 41-69% yields (Scheme 12.47) [85], Acids 161 were obtained after subsequent oxidation of the cycloadducts 160 with potassium permanganate. 

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