Nucleophilic addition to substituted 1H‐4,5‐dihydroimidazolium salts

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Abstract
1H‐4,5‐Dihydroimidazolium salts 1 react readily with nucleophilic reagents originating cyclic products which may be stable or become transformed into acyclic compounds maintaining the structural ethylenediamine unit. With methylmagnesium iodide compound 1e affords the expected imidazolidine, but in the case of substituted 1‐aryl‐3‐methyl‐2‐phenyl salts 1b‐d the N‐aryl‐N′‐methylethylenediamines 3b‐d and acetophenone (4) were isolated, the process representing the transfer of the C‐2 unit to a nucleophilic carbon. With alkaline cyanides salts 1 react efficiently affording α,α‐diaminonitriles 5. In these compounds the cyano group may be readily substituted by nucleophiles (hydroxyl anion, species with nucleophilic carbon and reagents that act by hydride ion transfer), in a way similar to the salts but with better yields.