The reaction of β-chloro imines 4 with potassium cyanide in methanol or with lithium aluminium hydride in dry ether gave rise to 2-cyanoazetidines 5 and azetidines 21. The reaction proceeded by nucleophilic addition of cyanide or hydride across the carbon- nitrogen double bond, followed by ringclosure. The corresponding β-chloro tosylhydrazones, which could either give rise to a four-or five-membered heterocycle on ...
