Abstract
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)NH 2, ketones RCOR′ and tertiary alcohol R 3 COH. The glycinonitrile is obtained via two successive additions on one of the cyano groups of cyanogen and is stable only when R = R′ = C 6H 5. 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 R 3COH 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).
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