Anthracene, bromination Diels-Alder additions

The reactivity criterion is less than satisfactory since many compounds that are generally recognized cis aromatic are quite reactive. For example, both phenanthrene and anthracene will add bromine, and anthracene will undergo Diels—Alder additions. The bond length criterion is also not quite satisfactory since compounds such a naphthalene, anthracene, and phenanthrene have a range of bond lengths. ... 

HEP readily reacts with hydrogen, chlorine, and bromine (but not iodine), by an addition reaction similar to other olefins [57-59]. Similarly, HE, HCl, and HER (but not HI), add to HEP. By reacting HEP with alcohols, mercaptans, and ammonia, hexafluoro ethers (CF3CFHCF20R), hexafluoro sulfides (CF3CFHCF2SR), and tetrafluoropropionitrile (CF3CFHCN) are obtained. Diels-Alder adducts have been identified fi om the reaction of anthracene, butadiene, and cyclopentadiene with HEP. Cyclic dimers of HEP can be prepared at 250-400°C under autogenous pressure [49]. Linear dimers and trimers of HEP can be produced catalytically in the presence of alkali metal halides in dimethylacetamide [48]. 

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