Reaction of Electrophilic Allyl Halides with Amines: A Reinvestigation
2006
The Michael-induced ring closure (MIRC) of amines with 2-bromoalkylidenemalonates has been reinvestigated and the reaction products with primary amines have been identified as (2-iminoethyl)malonates and not 2-aminoalkylidenemalonates as previously reported. The (2-iminoethyl)malonates are formed by ring opening of the intermediate unstable 2-aminocyclopropane-1,1-di-carboxylates (β-ACCs) and were characterized spectroscopically and via chemical transformation.
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