Metallation of Aldimines by Sodamide in Liquid Ammonia

Subsequent alkylation with hexyl bromide and cyclopentyl bromide. 

Apparatus 1-1, three-necked, round-bottomed flask, equipped with a dropping funnel, a mechanical stirrer and a gas-outlet (rubber stopper with a hole of 7 mm) 

Although we had good results in some subsequent reactions with alkyl halides, the metallation of imines by alkali amides has a limited applicability. We assume, on the basis of our results, that the pK values of the imines are close to that of ammonia. Thus, the reaction with alkali amides in this solvent will give rise to certain 

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