The cycloaddition reaction of acenaphthylene with coumalic acid, its methyl ester, or 4,6-dimethylcoumalic acid, with loss of carbon dioxide from the bridge, afforded a 2 : 1 adduct and a fluoranthene-8-carboxylic acid. The corresponding reaction with 3,6-disubstituted s-tetrazines gave 8,9-diazafluoranthene derivatives. Mechanisms are discussed.
T. Sasaki, K. Kanematsu and T. Hiramatsu, J. Chem. Soc., Perkin Trans. 1, 1974, 1213 DOI: 10.1039/P19740001213
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