Functionalized pentamethylferrocenes: Synthesis, structure, and electrochemistry

The advantageous properties of the Cp * ligand — intensified electron donation, steric bulk, and enhanced solubility in comparison to the ubiquitous Cp ligand — are finding increasing use in organometallic chemistry. A systematic evaluation of synthetic routes to pentamethylferrocene compounds with...

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Bibliographic Details
Published in:Journal of organometallic chemistry 1997-08, Vol.540 (1), p.127-145
Main Authors: Bildstein, Benno, Hradsky, Andreas, Kopacka, Holger, Malleier, Richard, Ongania, Karl-Hans
Format: Article
Language:English
Subjects:
Electrochemistry
Ferrocene
Iron
Pentamethylferrocene
X-ray structure
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Summary:The advantageous properties of the Cp * ligand — intensified electron donation, steric bulk, and enhanced solubility in comparison to the ubiquitous Cp ligand — are finding increasing use in organometallic chemistry. A systematic evaluation of synthetic routes to pentamethylferrocene compounds with a wide range of functionalities, including carboxyl, carbonyl, aminomethyl, vinyl, ethynyl, fulvenyl, cyclopentadienylmethyl, and others is reported. Spectroscopic, structural, and electrochemical properties of such functionalized pentamethylferrocenes Fc */2—R are compared to those of non-methylated ferrocenes Fc—R. The electronic influence of the Cp * ligand in these unsymmetricalferrocenes Fc */2—R has been studied by cyclic voltammetry measurements, demonstrating a decrease in oxidation potential of −0.276 V in direct comparison to non-methylated ferrocenes Fc—R.
ISSN:0022-328X
1872-8561
DOI:10.1016/S0022-328X(97)00133-2