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Issue 20, 2014
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Friedel–Crafts functionalization of the cyclopentadienyl ligand in buckymetallocenes

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Abstract

Acylated buckyferrocene and ruthenocene, Fe(η5-C60Me5)(η5-C5H4COR) (R = Me, Ph, and CH[double bond, length as m-dash]CHPh) and Ru(η5-C60Me5)(η5-C5H4COR) (R = Me and Ph), were obtained by Friedel–Crafts acylation of the parent buckymetallocenes with the corresponding acid chlorides and aluminum chloride in carbon disulfide at ambient temperature. The electron withdrawing and sterically hindered nature of the acyl groups were revealed by X-ray crystallography, infrared spectroscopy and electrochemical measurements. The possibility of further derivatizing the acylated products was illustrated by the conversion of the acetyl buckyruthenocene into the corresponding hydroxy and acetoxy compounds Ru(η5-C60Me5)(η5-C5H4CH(OH)Me) and Ru(η5-C60Me5)(η5-C5H4CH(OAc)Me).

Graphical abstract: Friedel–Crafts functionalization of the cyclopentadienyl ligand in buckymetallocenes

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Supplementary files

Article information


Submitted
24 Jul 2013
Accepted
24 Sep 2013
First published
24 Sep 2013

Dalton Trans., 2014,43, 7407-7412
Article type
Paper

Friedel–Crafts functionalization of the cyclopentadienyl ligand in buckymetallocenes

Y. Matsuo, Y. Kuninobu, S. Ito, M. Sawamura and E. Nakamura, Dalton Trans., 2014, 43, 7407
DOI: 10.1039/C3DT52002A

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