An unusual norbornadiene coupling product: Synthesis, characterization, and structure of the ruthenocene (C5Me5)Ru(η5-C5H 4C9H11)

Julia L. Brumaghim; Gregory S. Girolami

doi:10.1016/S0022-328X(99)00256-9

An unusual norbornadiene coupling product: Synthesis, characterization, and structure of the ruthenocene (C₅Me₅)Ru(η⁵-C₅H ₄C₉H₁₁)

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

Abstract

Treatment of (C₅Me₅)₂Ru₂Cl₄ with excess norbornadiene (NBD) in refluxing ethanol yields the substituted ruthenocene complex (C₅Me₅)Ru(η⁵-C₅H ₄C₉H₁₁), which possesses a cyclopentadienyl (Cp) ring bearing a tricyclo[4.2.1.0^2,5]-non-7-en-3-yl substituent. This compound has been characterized by NMR spectroscopy and X-ray crystallography. The substituted Cp ring is formed by coupling of two NBD units, C-C bond cleavage, migration of one hydrogen atom from one carbon atom to another, and loss of a hydrogen atom (presumably as HCl). Crystal data: monoclinic, space group P2₁/n, with a=10.0285(5), b=9.1801(5), c=21.249(1) Å, β=95.327(1)°, V=1947.9(2) Å³, Z=4, wR₂=0.0580 for 4611 data and 291 parameters.

Original language	English (US)
Pages (from-to)	258-262
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	586
Issue number	2
DOIs	https://doi.org/10.1016/S0022-328X(99)00256-9
State	Published - Sep 5 1999

Keywords

Group 8
Norbornadiene
Ring-opening metathesis polymerization
Ruthenium
Ruthenocene

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

Online availability

10.1016/S0022-328X(99)00256-9

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Cite this

@article{81d760aeba1343ca8e16f7dcabb28b28,

title = "An unusual norbornadiene coupling product: Synthesis, characterization, and structure of the ruthenocene (C5Me5)Ru(η5-C5H 4C9H11)",

abstract = "Treatment of (C5Me5)2Ru2Cl4 with excess norbornadiene (NBD) in refluxing ethanol yields the substituted ruthenocene complex (C5Me5)Ru(η5-C5H 4C9H11), which possesses a cyclopentadienyl (Cp) ring bearing a tricyclo[4.2.1.02,5]-non-7-en-3-yl substituent. This compound has been characterized by NMR spectroscopy and X-ray crystallography. The substituted Cp ring is formed by coupling of two NBD units, C-C bond cleavage, migration of one hydrogen atom from one carbon atom to another, and loss of a hydrogen atom (presumably as HCl). Crystal data: monoclinic, space group P21/n, with a=10.0285(5), b=9.1801(5), c=21.249(1) {\AA}, β=95.327(1)°, V=1947.9(2) {\AA}3, Z=4, wR2=0.0580 for 4611 data and 291 parameters.",

keywords = "Group 8, Norbornadiene, Ring-opening metathesis polymerization, Ruthenium, Ruthenocene",

author = "Brumaghim, {Julia L.} and Girolami, {Gregory S.}",

note = "Funding Information: We thank the Department of Energy (Grant DEFG02-96-ER45439) for support of this work, and Dr Scott Wilson and Teresa Prussak-Wieckowska of the University of Illinois Materials Chemistry Laboratory for collecting the X-ray data set. J.L.B. thanks the University of Illinois for a departmental fellowship. ",

year = "1999",

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doi = "10.1016/S0022-328X(99)00256-9",

language = "English (US)",

volume = "586",

pages = "258--262",

journal = "Journal of Organometallic Chemistry",

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TY - JOUR

T1 - An unusual norbornadiene coupling product

T2 - Synthesis, characterization, and structure of the ruthenocene (C5Me5)Ru(η5-C5H 4C9H11)

AU - Brumaghim, Julia L.

AU - Girolami, Gregory S.

N1 - Funding Information: We thank the Department of Energy (Grant DEFG02-96-ER45439) for support of this work, and Dr Scott Wilson and Teresa Prussak-Wieckowska of the University of Illinois Materials Chemistry Laboratory for collecting the X-ray data set. J.L.B. thanks the University of Illinois for a departmental fellowship.

PY - 1999/9/5

Y1 - 1999/9/5

N2 - Treatment of (C5Me5)2Ru2Cl4 with excess norbornadiene (NBD) in refluxing ethanol yields the substituted ruthenocene complex (C5Me5)Ru(η5-C5H 4C9H11), which possesses a cyclopentadienyl (Cp) ring bearing a tricyclo[4.2.1.02,5]-non-7-en-3-yl substituent. This compound has been characterized by NMR spectroscopy and X-ray crystallography. The substituted Cp ring is formed by coupling of two NBD units, C-C bond cleavage, migration of one hydrogen atom from one carbon atom to another, and loss of a hydrogen atom (presumably as HCl). Crystal data: monoclinic, space group P21/n, with a=10.0285(5), b=9.1801(5), c=21.249(1) Å, β=95.327(1)°, V=1947.9(2) Å3, Z=4, wR2=0.0580 for 4611 data and 291 parameters.

AB - Treatment of (C5Me5)2Ru2Cl4 with excess norbornadiene (NBD) in refluxing ethanol yields the substituted ruthenocene complex (C5Me5)Ru(η5-C5H 4C9H11), which possesses a cyclopentadienyl (Cp) ring bearing a tricyclo[4.2.1.02,5]-non-7-en-3-yl substituent. This compound has been characterized by NMR spectroscopy and X-ray crystallography. The substituted Cp ring is formed by coupling of two NBD units, C-C bond cleavage, migration of one hydrogen atom from one carbon atom to another, and loss of a hydrogen atom (presumably as HCl). Crystal data: monoclinic, space group P21/n, with a=10.0285(5), b=9.1801(5), c=21.249(1) Å, β=95.327(1)°, V=1947.9(2) Å3, Z=4, wR2=0.0580 for 4611 data and 291 parameters.

KW - Group 8

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KW - Ring-opening metathesis polymerization

KW - Ruthenium

KW - Ruthenocene

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