# Ferrole

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{{Short description|Class of chemical compounds}}
thumb|Structure of the ferrole Fe<sub>2</sub>C<sub>4</sub>H<sub>4</sub>(CO)<sub>6</sub>.<ref>{{cite journal|doi=10.1016/S0022-328X(00)82143-9|title=Kristallstruktur, <sup>1</sup>H-NMR- und Massenspektrum von Tricarbonylferracyclopentadien-tricarbonyleisen, C<sub>4</sub>H<sub>4</sub>Fe<sub>2</sub>(CO)<sub>6</sub>|year=1976|last1=Dettlaf|first1=Gerd|last2=Weiss|first2=Erwin|journal=Journal of Organometallic Chemistry|volume=108|issue=2|pages=213–223}}</ref> Color scheme: red = O, gray = C, dark blue = Fe, white = H.
{{confuse| Ferrule}}
In [organoiron chemistry](/source/organoiron_chemistry), a '''ferrole''' is a type of diiron complex containing the (OC)<sub>3</sub>FeC<sub>4</sub>R<sub>4</sub> heterocycle that is [pi-bond](/source/pi-bond)ed to a Fe(CO)<sub>3</sub> group.  These compounds have Fe-Fe bonds (ca. 252 [pm](/source/picometer)) and semi-bridging CO ligands (Fe-C distances = 178, 251 pm).  They are typically air-stable, soluble in nonpolar solvents, and red-orange in color.<ref>{{cite book|doi=10.1016/B978-008046518-0.00051-9|chapter=Dinuclear Iron Compounds with Hydrocarbon Ligands|title=Comprehensive Organometallic Chemistry|year=1982|last1=Fehlhammer|first1=W.P.|last2=Stolzenberg|first2=H.|pages=513–613|isbn=9780080465180|editor1=Geoffrey Wilkinson|editor2=F. Gordon A. Stone|editor3=Edward W. Abel}}</ref>
==Synthesis==
Ferroles typically arise by the reaction of [alkyne](/source/alkyne)s with [iron carbonyl](/source/iron_carbonyl)s.  Such reactions are known to generate many products, e.g. complexes of [cyclopentadienone](/source/cyclopentadienone)s and para-[quinone](/source/quinone)s.<ref>{{cite book|title=Organic Syntheses via Metal Carbonyls Volume 1|year=1968|editor1=Piero Pino|editor2=Irving Wender|publisher=Wiley Interscience|location=NY}}</ref><ref>{{cite journal |doi=10.1021/cr60218a001|title=Synthesis of Organic Compounds by Direct Carbonylation Reactions Using Metal Carbonyls |year=1962 |last1=Bird |first1=C. W. |journal=Chemical Reviews |volume=62 |issue=4 |pages=283–302 }}</ref>

Another route involves the desulfurization of thiophenes (SC<sub>4</sub>R<sub>4</sub>) by iron carbonyls, shown in the following idealized equation:
:Fe<sub>3</sub>(CO)<sub>12</sub>  +  SC<sub>4</sub>R<sub>4</sub>  →  Fe<sub>2</sub>(CO)<sub>6</sub>C<sub>4</sub>R<sub>4</sub>  +  FeS  + 6{{nbsp}}CO

An unusual route to ferroles involves treatment of [Collman's reagent](/source/Collman's_reagent) with trimethylsilyl chloride (tms =  (CH<sub>3</sub>)<sub>3</sub>Si):
:2{{nbsp}}Na<sub>2</sub>Fe(CO)<sub>4</sub>  +  4{{nbsp}}tmsCl  →  Fe<sub>2</sub>(CO)<sub>6</sub>C<sub>4</sub>(Otms)<sub>4</sub>  +  2{{nbsp}}CO  +  4{{nbsp}}NaCl

==Reactions==
Some ferroles  react with tertiary phosphines to give the substituted [flyover complex](/source/flyover_complex) Fe<sub>2</sub>(CO)<sub>5</sub>(PR<sub>3</sub>)(C<sub>4</sub>R<sub>4</sub>CO).<ref>{{cite journal |doi=10.1016/0022-328X(95)05936-J|title=Reactions of the 'ferrole' complex [Fe2(CO)6(C2Et2)2] with group 15 donor ligands and with alkynes. Stepwise formation and disengagement of tropones. Crystal and molecular structure of [Fe2(CO)5{(CEt)2 CO(CEt)2 CHCPH}]|year=1996|last1=Giordano|first1=Roberto|last2=Sappa|first2=Enrico|last3=Cauzzi|first3=Daniele|last4=Predieri|first4=Giovanni|last5=Tiripicchio|first5=Antonio|journal=Journal of Organometallic Chemistry|volume=511|issue=1–2|pages=263–271}}</ref><ref>{{cite book |doi=10.1016/B978-008046519-7.00058-7|chapter=Dinuclear Iron Compounds with Hydrocarbon Ligands|title=Comprehensive Organometallic Chemistry II|year=1995|last1=Fagan|first1=Paul J.|pages=231–258|isbn=9780080465197}}</ref>

==References==
<references />

Category:Organoiron compounds
Category:Carbonyl complexes
Category:Trimethylsilyl compounds

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Adapted from the Wikipedia article [Ferrole](https://en.wikipedia.org/wiki/Ferrole) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Ferrole?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.