The chemistry of cyanoacetylenes. Part I. Reactions of nitrilium ions conjugated with acetylene

Abstract

Although chlorocyanoacetylene is converted into an amide in sulphuric acid, cyanoacetylene itself is not. Nevertheless, both nitriles undergo the Ritter reaction with olefins and alcohols. N-(1,1-Dimethyl-2-chloroethyl)-propiolamide, one of the Ritter reaction products, gives an oxazoline on treatment with alkoxide, with accompanying addition of the alkoxide to the triple bond.