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

Michael F. Mayer, Qinwei Wang, M. Mahmun Hossain

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

The reason for the apparent cis-aziridine selectivity in the reaction of ethyl diazoacetate with N-benzylidene aniline, catalyzed by [(η5-C5H5)(CO)2Fe(THF)] +[BF4]-, is reported. The catalytic reaction produces both cis and trans-aziridines. Once the imine has been consumed, the trans-isomer is shown to undergo a catalytic decomposition, leaving cis-aziridine and by-products. The reaction is graphically profiled to illustrate the relative quantity of reactants and products as a function of time. A new mechanistic model is proposed in order to explain the observed selectivity.

Original languageEnglish
Pages (from-to)78-83
Number of pages6
JournalJournal of Organometallic Chemistry
Volume630
Issue number1
DOIs
StatePublished - Jul 2 2001

Keywords

  • Aziridines
  • Ethyl diazoacetate
  • Imines
  • Iron Lewis acid

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