A SIMPLE SYNTHETIC METHOD OF [3.3]AZACYCLOPHANES BY ALKYLATION OF CYANAMIDE

Dialkylation reaction of commercially available cyanamid with the corr esponding bromomethyl compounds proceeds smoothly in the presence of a phase-transfer catalyst in a mixture of toluene-water or dichlorometh ane-water under mild alkaline conditions, and affords N,N'-dicyano[3.3 ]azacyclophanes and their higher homologs in good to moderate yields. The two-step reaction involving the coupling followed by decyanation o f the N-cyano groups provides a new, simple, synthetic method of azacy clophanes, especially for the sterically constrained or acid sensitive azacyclphanes.