Ethylene acetal, dicyanoketene

The synthesis of dicyanoketene ethylene acetal described here is a slight modification of one published recently.3 The procedure has been applied successfully to the synthesis of dicyanoketene dimethyl acetal and dicyanoketene diethyl acetal.3... 

Dicyanoketene ethylene acetal reacts with tertiary amines to give quaternary ammonium inner salts.3 Similarly, it reacts with sulfides to give sulfonium inner salts.3 These products are generally solids that can be used to characterize tertiary amines, and sulfides. Dicyanoketene acetals can be converted to pyrimidines, pyrazoles, or isoxazoles in one step.4... 

Some urea dissolved in anhydrous ethylene glycol, then finely divided tetracyanoethylene added, and heated ca. 15 min. at 70-75° on a steam bath with stirring until soln. is complete dicyanoketene ethylene acetal. Y 77-i F. e. s. C. L. Dickinson and L. R. Melby, Org. Synth. 39, 13 (1959). 

Copolymeriziation of polystyrene-bound dicyanoketene acetal (DCKA) and ethylene glycol dimethacrylate (EGDMA) yielded a polymer (41) with high n -acidity. It was found to be an effective and completely recyclable catalyst in the high yielding carbon-carbon bond-forming reaction of dimethylacetals with silylated nucleophiles (Scheme 4.26) [118]. 

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