REACTIONS OF ORGANOMETALLIC COMPOUNDS WITH CYANOGEN

Treatment of 2 mol of organometallic compounds RM and R′M′ with 1 mol of cyanogen (CN)2 gives a mixture of glycinonitriles RR′C(CN)NH2, ketones RCOR′ and tertiary alcohol R3 COH. The glycinonitrile is obtained via two successive additions on one of the cyano groups of cyanogen and is stable only when R = R′ = C6H5. When R = R′ = alkyl, the intermediate obtained is unstable and undergoes either elimination of metallic cyanide to give ketones RCOR′, or substitution of the cyano group to give the carbinols R3COH through a non-isolated carbimine. Organolithium compounds favour the elimination reaction and excess of organometallic favours the glycinonitrile (if stable) or the substitution reaction (if not). © 1979.