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DOI:
10.1055/sos-SD-019-00155
North, M., Science of Synthesis, (2004) 19, 266.
The addition of cyanide to a ketone is a more difficult task than the corresponding addition to an aldehyde. Two factors, steric hindrance and the electron-donating effect of alkyl substituents, combine to make the carbonyl carbon of a ketone less reactive than that of an aldehyde. Hence, the equilibrium between the ketone and cyanohydrin is often not favorable for cyanohydrin synthesis. To avoid this problem, cyanohydrin derivatives of ketones are often prepared using reagents such as trimethylsilyl cyanide, for which the reaction is irreversible.
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