Reaction of 9-Diazofluorene with 2,3-Dichloro-5,6-dicyano-p-benzoquinone: The Structure and the Behaviors of Resulting Product

Article abstract of DOI:10.1246/bcsj.62.444

The title reaction gave 3',4'-dichloro-1',6'-dicyanospironorcarene>-2',5'-dione (2) in a good yield.Recrystallization of 2 from solvents such as benzene, dioxane, acetonitrile, and acetone gave each molecular complex consisting of a 2/solvent molar ratio of 1:1.The structure of 2 was determined by the use of one complex, 2*CH3COCH3, by X-ray crystallographic analysis, which revealed that an interaction between 2 and acetone was not very strong.Such a host-guest interaction was shown also from 1H NMR spectroscopy and a differential thermal analysis of the complex.Compound 2 afforded the corresponding spiroacetals of 9-fluorenone through reactions with ethylene glycol and 1,3-propanediol.