Abstract
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 treatment with potassium cyanide in methanol, were shown to afford N-tosylamino 2-cyanoazetidines, exclusively.
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