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Reaction of an Iron(IV) Nitrido Complex with Cyclohexadienes: Cycloaddition and Hydrogen-Atom Abstraction
Journal article   Open access   Peer reviewed

Reaction of an Iron(IV) Nitrido Complex with Cyclohexadienes: Cycloaddition and Hydrogen-Atom Abstraction

Wei-Tsung Lee, Ruth A. Juarez, Jeremiah J. Scepaniak, Salvador B. Munoz, Diane A. Dickie, Haobin Wang and Jeremy M. Smith
Inorganic chemistry, v 53(16), pp 8425-8430
18 Aug 2014
PMID: 25068927
url
https://doi.org/10.1021/ic5010006View
Published, Version of Record (VoR) Open

Abstract

Chemistry Chemistry, Inorganic & Nuclear Physical Sciences Science & Technology
The iron(IV) nitrido complex PhB(MesIm)(3)Fe N reacts with 1,3-cyclohexadiene to yield the iron(II) pyrrolide complex PhB-(MesIm)(3)Fe(eta(5)-C4H4N) in high yield. The mechanism of product formation is proposed to involve sequential [4 + 1] cycloaddition and retro Diels-Alder reactions. Surprisingly, reaction with 1,4-cyclohexadiene yields the same iron-containing product, albeit in substantially lower yield. The proposed reaction mechanism, supported by electronic structure calculations, involves hydrogen-atom abstraction from 1,4-cydohexadiene to provide the cyclohexadienyl radical. This radical is an intermediate in substrate isomerization to 1,3-cyclohexadiene, leading to formation of the pyrrolide product.

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Collaboration types
Domestic collaboration
Web of Science research areas
Chemistry, Inorganic & Nuclear
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