Diane Dickie - Styrene Aziridination by Iron(IV) Nitrides.

Document created by Diane Dickie on Nov 17, 2015
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  Munoz, Salvador B., III, Lee, Wei-Tsung, Dickie, Diane A.,   Scepaniak, Jeremiah J., Subedi, Deepak, Pink, Maren, Johnson,   Michael D., Smith, Jeremy M. Angewandte Chemie, International   Edition 54 (36) 10600-10603

  Abstract: Thermolysis of the iron(IV) nitride   complex [PhB(tBuIm)3Fe≡N] with styrene leads to formation of the   high-spin iron(II) aziridino complex [PhB(tBuIm)3Fe-N(CH2CHPh)].   Similar aziridination occurs with both electron-rich and   electron-poor styrenes, while bulky styrenes hinder the reaction.   The aziridino complex [PhB(tBuIm)3Fe-N(CH2CHPh)] acts as a   nitride synthon, reacting with electron-poor styrenes to generate   their corresponding aziridino complexes, i.e., aziridine   cross-metathesis. Reaction of [PhB(tBuIm)3Fe-N(CH2CHPh)] with   Me3SiCl releases the N-functionalized aziridine Me3SiN(CH2CHPh)   while simultaneously generating [PhB(tBuIm)3FeCl]. This closes a   synthetic cycle for styrene aziridination by a nitride complex.   While the less hindered iron(IV) nitride complex   [PhB(MesIm)3Fe≡N] reacts with styrenes below room temp., only   bulky styrenes lead to tractable aziridino products. [on   SciFinder(R)]

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