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

Abstract

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.

Key words

aziridines - cyclization - aminocyclopropanes - DFT calculations - vinylic S_N2

• References and Notes


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