Friedel-Crafts functionalization of the cyclopentadienyl ligand in buckymetallocenes

Yutaka Matsuo; Yoichiro Kuninobu; Shingo Ito; Masaya Sawamura; Eiichi Nakamura

doi:10.1039/c3dt52002a

Friedel-Crafts functionalization of the cyclopentadienyl ligand in buckymetallocenes

Yutaka Matsuo, Yoichiro Kuninobu, Shingo Ito, Masaya Sawamura, Eiichi Nakamura

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

Acylated buckyferrocene and ruthenocene, Fe(η⁵-C ₆₀Me₅)(η⁵-C₅H₄COR) (R = Me, Ph, and CHCHPh) and Ru(η⁵-C₆₀Me ₅)(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-C ₅H₄CH(OH)Me) and Ru(η⁵-C ₆₀Me₅)(η⁵-C₅H ₄CH(OAc)Me). This journal is

Original language	English
Pages (from-to)	7407-7412
Number of pages	6
Journal	Dalton Transactions
Volume	43
Issue number	20
DOIs	https://doi.org/10.1039/c3dt52002a
Publication status	Published - May 28 2014
Externally published	Yes

All Science Journal Classification (ASJC) codes

Inorganic Chemistry

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title = "Friedel-Crafts functionalization of the cyclopentadienyl ligand in buckymetallocenes",

abstract = "Acylated buckyferrocene and ruthenocene, Fe(η5-C 60Me5)(η5-C5H4COR) (R = Me, Ph, and CHCHPh) and Ru(η5-C60Me 5)(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-C 5H4CH(OH)Me) and Ru(η5-C 60Me5)(η5-C5H 4CH(OAc)Me). This journal is",

author = "Yutaka Matsuo and Yoichiro Kuninobu and Shingo Ito and Masaya Sawamura and Eiichi Nakamura",

year = "2014",

month = may,

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doi = "10.1039/c3dt52002a",

language = "English",

volume = "43",

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journal = "Dalton Transactions",

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T1 - Friedel-Crafts functionalization of the cyclopentadienyl ligand in buckymetallocenes

AU - Matsuo, Yutaka

AU - Kuninobu, Yoichiro

AU - Ito, Shingo

AU - Sawamura, Masaya

AU - Nakamura, Eiichi

PY - 2014/5/28

Y1 - 2014/5/28

N2 - Acylated buckyferrocene and ruthenocene, Fe(η5-C 60Me5)(η5-C5H4COR) (R = Me, Ph, and CHCHPh) and Ru(η5-C60Me 5)(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-C 5H4CH(OH)Me) and Ru(η5-C 60Me5)(η5-C5H 4CH(OAc)Me). This journal is

AB - Acylated buckyferrocene and ruthenocene, Fe(η5-C 60Me5)(η5-C5H4COR) (R = Me, Ph, and CHCHPh) and Ru(η5-C60Me 5)(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-C 5H4CH(OH)Me) and Ru(η5-C 60Me5)(η5-C5H 4CH(OAc)Me). This journal is

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DO - 10.1039/c3dt52002a

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JO - Dalton Transactions

JF - Dalton Transactions

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ER -

Friedel-Crafts functionalization of the cyclopentadienyl ligand in buckymetallocenes

Abstract

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