Mechanism of Gas Phase Cyanation of Alkenes and Aromatics

Article abstract of DOI:10.1021/ja00347a049

ICN was photolyzed at 254 nm in the gas phase in the presence of 15-20 torr of certain alkenes or aromatics.The products were analyzed by GC-MS.Ethene gave acrylonitrile; propene gave acrylonitrile, allyl cyanide and cis- and trans-1-cyanopropene; 2-methylpropene gave 2 cyanopropene; benzene gave benzonitrile; toluene gave benzonitrile and 2-, 3-, and 4-cyanotoluene.These products are explained by a mechanism involving attack of CN on the organic to give vibrationally excited radicals.These radicals rapidly fragment, producing the major products, or react more slowly in bimolecular processes.The relevance of these results to RF discharge chemistry is discussed.