An explanation for the apparent cis-aziridine selectivity in the iron Lewis acid-catalyzed reaction of N-benzylidene aniline and ethyl diazoacetate

The reason for the apparent cis-aziridine selectivity in the reaction of et hyl diazoacetate with N-benzylidene aniline, catalyzed by [(eta (5)-C5H5)(C O)(2)Fe(THF)](+)[BF4](-), is reported. The catalytic reaction produces both cis and traps-aziridines. Once the in-line has been consumed, the traps-is omer is shown to undergo a catalytic decomposition, leaving cis-aziridine a nd by-products. The reaction is graphically profiled to illustrate the rela tive quantity of reactants and products as a function of time. A new mechan istic model is proposed in order to explain the observed selectivity. (C) 2 001 Elsevier Science B.V. All rights reserved.