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In situ formation of HCN can be sourced using precursors such as acetone cyanohydrin. Alternatively, cyano-silyl derivatives such as TMS-CN allows for both the cyanation and protection in one step without the need for HCN. [6] Similar procedures relying on ester, phosphate and carbonate formation have been reported. [7] [8] [9]
In transhydrocyanation, an equivalent of HCN is transferred from a cyanohydrin, e.g. acetone cyanohydrin, to another HCN acceptor. The transfer is an equilibrium process, initiated by base. The reaction can be driven by trapping reactions or by the use of a superior HCN acceptor, such as an aldehyde. [6]
Glycolonitrile polymerizes under alkaline conditions above pH 7.0. As the product of polymerization is an amine with a basic character, the reaction is self-catalysed, gaining in speed with ongoing conversion. Glycolonitrile can react with ammonia to give aminoacetonitrile, which can be hydrolysed to give glycine:
Another synthetic pathway for α-hydroxy acids involves the addition of hydrogen cyanide to ketones or aldehydes, followed by the acidic hydrolysis of the cyanohydrin intermediate. [14] R−CHO + HCN → R−CH(OH)CN R−CH(OH)CN + 2H 2 O → R−CH(OH)CO 2 H + NH 3
Acetone cyanohydrin is an intermediate en route to methyl methacrylate. [6] Treatment with sulfuric acid gives the sulfate ester of the methacrylamide, [clarification needed] methanolysis of which gives ammonium bisulfate and methyl methacrylate. [7] It is used as a surrogate in place of HCN, as illustrated by its use as a precursor to lithium ...
In organic chemistry, a cyanohydrin reaction is an organic reaction in which an aldehyde (−CH=O) or ketone (>C=O) reacts with a cyanide anion ...
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Cyanogen is typically generated from cyanide compounds. One laboratory method entails thermal decomposition of mercuric cyanide: . 2 Hg(CN) 2 → (CN) 2 + Hg 2 (CN) 2 Or, one can combine solutions of copper(II) salts (such as copper(II) sulfate) with cyanides; an unstable copper(II) cyanide is formed which rapidly decomposes into copper(I) cyanide and cyanogen.