Abstract
On heating with sodium cyanide in aqueous or ethanolic solution α, β-dimethyl-glycidonitrile (I) affords α-acetylpropionitrile. In order to elucidate this reaction mechanism α-ethyl-β-methylglycidonitrile (VI) was boiled with sodium cyanide in aqueous solution and only 2-cyanopentan-3-one (VIII) was obtained and not its isomer, 3-cyanopentan-2-one (VII). (I) was boiled with a labelled sodium cyanide, Na14CN, in aqueous or methanolic solution and a radioactive α-acetylpropionitrile (IX) was obtained. The specific activity of its 2, 4-dinitrophenylhydrazone (X) was equal to that of Na14CN used as the starting material. From these facts, the mechanism of this reaction was clarified to be the initial addition of sodium cyanide to (I) to form cyanohydrin of (II) which underwent decomposition to form (II), and not the rearrangement of a proton or -CN group of (I).
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