Perylenes cycloaddition

The gas-phase 4- -2-cycloaddition of benzyne with perylene produced naphtho[l,2,3,4- fti]perylene under solvent-free conditions. The microwave-catalysed reaction of A-(2,4-dicyano-l,5-dimethyl-3-phenylcyclopenta-2,4-dienyl) 2,2,2-trifluoroacetamide with alkynes formed bicyclic and polycyclic compounds. The Diels-Alder reaction of maldoxin (67) with an isopropenylallene (68) yielded a cycloadduct (69) closely related to chloropestolide A and a second adduct, which... 

Diels-Alder cycloaddition provides one of the most useful methods for the construction of polycyclic aromatic ring systems. With the use of maleic anhydride as dienophile, two additional carbon atoms may be fused to the bay region sites of some polycyclic arylenes to generate additional rings. For example, the first step in the synthesis of benzo[ghi]perylene 6 involves a Diels-Alder cycloaddition between perylene and maleic anhydride (Scheme 3.5) [19]. Aryne intermediates generated in situ also serve as dienophiles for Diels-Alder cycloadditions for example, reaction of 1,5-naphthadiyne (generated in situ from 2,6-dibromo-l,5-bis[(p-tolylsulfonyl)oxy] naphthalene with 2-methylisoindole forms an adduct which upon oxidation with m-chloroperbenzoic acid affords dibenzo[fe,k]chrysene 7 (Scheme 3.5) [20]. 

Mullen and co-workers reported the synthesis and mesomorphic behavior of 2,9-dialkyl-5,6,ll,12-tetrahydrocoronene-5,6,ll,12-tetracarboxylic acid derivatives 83 [155,156], The synthesis of these compounds is presented in Scheme 4.22. Only a mono-cycloaddition product of dienophiles to perylene was observed under normal conditions. However, the bisaddition product could be produced under drastic conditions, but only in low yield, which is attributable to the lower solubility... 

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