Cinnamic acid acyl cyanides

Compared to the older procedures the use of acid iodides in acetonitrile or dichloromethane as solvent constituted a remarkable improvement. Aromatic and aliphatic acyl cyanides are accessible by this route. For example acyl cyanides of cinnamic acid and phenylacetic acid could be obtained in 33% and 49% yields. Copper(I) cyanide in diethyl ether in the presence of lithium iodide gave a-cyano ketones in 50-70%. The reaction can be carried out at room temperature in diethyl ether or slightly above or at 80 C in acetonitrile. It is not possible to obtain the acyl cyanide from acryloyl chloride, chloroformate or oxalyl chloride by this approach. 

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