Everything about Cyclobutadieneiron Tricarbonyl totally explained
Cyclobutadieneiron tricarbonyl or (C
4H
4)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.
This compound reacts with
di-iron nonacarbonyl (obtained from
photolysis of
iron pentacarbonyl) to Cyclobutadieneiron tricarbonyl.
Cyclobutadieneiron tricarbonyl displays
aromaticity as evidenced by some of its reactions which can be classified as
electrophilic aromatic substitution :
»
It reacts in
Friedel-Crafts acylation with acetyl chloride and aluminium 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:
» Further Information
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