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

WeiTsung Lee | Zendy; Ruth A. Juarez | Zendy; Jeremiah J. Scepaniak | Zendy; Salvador B. Muñoz | Zendy; Diane A. Dickie | Zendy; Haobin Wang | Zendy; Jeremy M. Smith | Zendy

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

Author(s) -

WeiTsung Lee,

Ruth A. Juarez,

Jeremiah J. Scepaniak,

Salvador B. Muñoz,

Diane A. Dickie,

Haobin Wang,

Jeremy M. Smith

Publication year - 2014

Publication title -

inorganic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.348

H-Index - 233

eISSN - 1520-510X

pISSN - 0020-1669

DOI - 10.1021/ic5010006

Subject(s) - chemistry , cycloaddition , hydrogen atom abstraction , abstraction , medicinal chemistry , atom (system on chip) , hydrogen , stereochemistry , organic chemistry , catalysis , parallel computing , philosophy , epistemology , computer science

The iron(IV) nitrido complex PhB(MesIm)3Fe≡N reacts with 1,3-cyclohexadiene to yield the iron(II) pyrrolide complex PhB(MesIm)3Fe(η(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-cyclohexadiene 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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