The conversion of aldehydes and ketones via their 2,4,6-tri-isopropylbenzenesulphonyl hydrazones into nitrites containing one additional carbon atom

Abstract

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 yields. 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 of the nitriles.