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Cyclobutadieneiron tricarbonyl or (C4H4)Fe(CO)3 is an organometallic complex of cyclobutadiene and an iron metal carbonyl. The chemical compound is used in organic chemistry as a precursor for cyclobutadiene. It was first prepared in 1965 by Rowland Pettit starting from cyclooctatetraene    :
Cyclooctatetraene is chlorinated to the [4.0.2]-bicyclic compound which reacts further with the alkyne dimethyl acetylenedicarboxylate in a Diels-Alder reaction followed by a reverse-DA reaction by pyrolysis at 200°C releasing cis-dichlorocyclobutene.
It reacts in Friedel-Crafts acylation with acetyl chloride and aluminum chloride to the acyl derivative 2, with formaldehyde and hydrochloric acid to the chloromethyl derivative 3, in a Vilsmeier-Haack reaction with N-methylformanilide and phosphorus oxychloride to the formyl 4 and in a Mannich reaction to amine derivative 4
The reaction mechanism is identical to that of EAS:
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Cyclobutadieneiron_tricarbonyl". A list of authors is available in Wikipedia.|