Sodium Amide Induced Cyclization of 2-Iodoprop-2-enylamines: Application to the Synthesis of 1-Aryl-2-methyleneaziridines.

The effect of the halogen on the rate of sodium amide induced cyclization of 2-haloprop-2-enylamines to methyleneaziridines is studied. Using DFT calculations and competition experiments, it is shown to proceed faster using iodide-based substrates. A practical route to 1-aryl-2-methyleneaziridines is devised based on these observations and their further rearrangement to cyclopropanimines explored. [ABSTRACT FROM AUTHOR]