Scheme 16 Two exceptions using acylacetonitriles

Using aromatic compounds containing two acylacetonitrile functionalities led to the production of bis(dioxanyl)arenes at room temperature in moderate yields as shown in Scheme 15.

For the reaction of styrene with benzoylacetonitrile, 2-cyano- 1,4-diphenyl-butane-1,4-dione was isolated in 31% yield, while the reaction of 1,1-di-phenylethene with 2-(2-cyano-1-oxoethyl)-5-methylfuran gave 2-cyano-4,4-diphenylbutanolide in 83% yield and no 1,2-dioxanes were detected. Both exceptions are explained by the fact that the corresponding dioxane, once formed during the reaction, would be decomposed in acidic media (Scheme 16) [78,80,106].

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