Journal of the Chemical Society. Perkin transactions I p. 1487 - 1492 (1980)
Update date:2022-08-03
Topics:
Jiricny, Josef
Orere, Daniel M.
Reese, Colin B.
2,4,6-Tri-isopropylbenzenesulphonyl hydrazones of aliphatic and alicyclic aldehydes and ketones react readily with potassium cyanide in boiling methanol solution to give the corresponding nitriles (containing one more carbon atom than the original aldehyde or ketone) in satisfactory yield. Under the same conditions, benzaldehyde 2,4,6-tri-isopropylbenzenesulphonyl hydrazone gives phenylacetonitrile in very low yield.In some cases, the arenesulphonyl hydrazones may be generated in situ, in methanol solution, from the carbonyl compounds and 2,4,6-tri-isopropylbenzenesulphonohydrazide (11a), thereby constituting a one-pot preparation or the nitriles.
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