Synthesis of Ethylene Bridged Biscyclopentadiene Ligand Precursor Compounds and Some of their ansa-Zirconocene Derivatives Chiral Epoxides: A Synthetic Strategy of High Variability

Bernhard Rieger; Gerhard Jany; Manfred Steimann; Riad Fawzi

doi:10.1515/znb-1994-0404

Synthesis of Ethylene Bridged Biscyclopentadiene Ligand Precursor Compounds and Some of their ansa-Zirconocene Derivatives Chiral Epoxides: A Synthetic Strategy of High Variability

Bernhard Rieger, Gerhard Jany, Manfred Steimann, Riad Fawzi

University of Tübingen

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

19 Scopus citations

Abstract

The chiral ligand precursor systems [1-Cp¹-1-R¹-2-R-²-2-Cp²]ethane 5a–d bearing two different cyclopentadienyl fragments (Cp¹, Cp² = Cp, Ind, Flu) and a variable bridge substitution pattern (R¹, R² = H, Ph, cyclopentyl, cyclohexyl) were prepared starting from the corresponding epoxides. The solid state structures of six organic intermediates are reported in order to prove the stereochemistry of the ligand forming reactions. Treatment of the dilithio salts of 5a–d with ZrCl₄ in CH₂Cl₂ afforded chiral ansa-zirconocene dichlorides (6a–d).

Original language	English
Pages (from-to)	451-458
Number of pages	8
Journal	Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume	49
Issue number	4
DOIs	https://doi.org/10.1515/znb-1994-0404
State	Published - 1 Apr 1994
Externally published	Yes

Keywords

Biscyclopentadienes
Chiral Epoxides
Chiral ansa-Zirconocene Dichlorides
Fluorenyl Alcohols
Spirocyclopropanes

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10.1515/znb-1994-0404

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@article{8257123787e54becb9071674bad3003f,

title = "Synthesis of Ethylene Bridged Biscyclopentadiene Ligand Precursor Compounds and Some of their ansa-Zirconocene Derivatives Chiral Epoxides: A Synthetic Strategy of High Variability",

abstract = "The chiral ligand precursor systems [1-Cp1-1-R1-2-R-2-2-Cp2]ethane 5a–d bearing two different cyclopentadienyl fragments (Cp1, Cp2 = Cp, Ind, Flu) and a variable bridge substitution pattern (R1, R2 = H, Ph, cyclopentyl, cyclohexyl) were prepared starting from the corresponding epoxides. The solid state structures of six organic intermediates are reported in order to prove the stereochemistry of the ligand forming reactions. Treatment of the dilithio salts of 5a–d with ZrCl4 in CH2Cl2 afforded chiral ansa-zirconocene dichlorides (6a–d).",

keywords = "Biscyclopentadienes, Chiral Epoxides, Chiral ansa-Zirconocene Dichlorides, Fluorenyl Alcohols, Spirocyclopropanes",

author = "Bernhard Rieger and Gerhard Jany and Manfred Steimann and Riad Fawzi",

note = "Funding Information: We thank the Polymer Research Laboratory of BASF AG, D-67056 Ludwigshafen for gift of chemicals. The work of B. R. was made possible by the Fonds der Chemischen Industrie (Liebig-Stipendium) and the Deutsche Forschungsgemeinschaft by the award of fellowships. Generous financial support by the DFG (grant Ri 613/3-2) and by Professor Dr. E. Lindner (University of T{\"u}bingen) is also gratefully acknowledged.",

year = "1994",

month = apr,

day = "1",

doi = "10.1515/znb-1994-0404",

language = "English",

volume = "49",

pages = "451--458",

journal = "Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences",

issn = "0932-0776",

publisher = "Walter de Gruyter GmbH",

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}

Rieger, B, Jany, G, Steimann, M & Fawzi, R 1994, 'Synthesis of Ethylene Bridged Biscyclopentadiene Ligand Precursor Compounds and Some of their ansa-Zirconocene Derivatives Chiral Epoxides: A Synthetic Strategy of High Variability', Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, vol. 49, no. 4, pp. 451-458. https://doi.org/10.1515/znb-1994-0404

Synthesis of Ethylene Bridged Biscyclopentadiene Ligand Precursor Compounds and Some of their ansa-Zirconocene Derivatives Chiral Epoxides: A Synthetic Strategy of High Variability. / Rieger, Bernhard; Jany, Gerhard; Steimann, Manfred et al.
In: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, Vol. 49, No. 4, 01.04.1994, p. 451-458.

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

TY - JOUR

T1 - Synthesis of Ethylene Bridged Biscyclopentadiene Ligand Precursor Compounds and Some of their ansa-Zirconocene Derivatives Chiral Epoxides

T2 - A Synthetic Strategy of High Variability

AU - Rieger, Bernhard

AU - Jany, Gerhard

AU - Steimann, Manfred

AU - Fawzi, Riad

N1 - Funding Information: We thank the Polymer Research Laboratory of BASF AG, D-67056 Ludwigshafen for gift of chemicals. The work of B. R. was made possible by the Fonds der Chemischen Industrie (Liebig-Stipendium) and the Deutsche Forschungsgemeinschaft by the award of fellowships. Generous financial support by the DFG (grant Ri 613/3-2) and by Professor Dr. E. Lindner (University of Tübingen) is also gratefully acknowledged.

PY - 1994/4/1

Y1 - 1994/4/1

N2 - The chiral ligand precursor systems [1-Cp1-1-R1-2-R-2-2-Cp2]ethane 5a–d bearing two different cyclopentadienyl fragments (Cp1, Cp2 = Cp, Ind, Flu) and a variable bridge substitution pattern (R1, R2 = H, Ph, cyclopentyl, cyclohexyl) were prepared starting from the corresponding epoxides. The solid state structures of six organic intermediates are reported in order to prove the stereochemistry of the ligand forming reactions. Treatment of the dilithio salts of 5a–d with ZrCl4 in CH2Cl2 afforded chiral ansa-zirconocene dichlorides (6a–d).

AB - The chiral ligand precursor systems [1-Cp1-1-R1-2-R-2-2-Cp2]ethane 5a–d bearing two different cyclopentadienyl fragments (Cp1, Cp2 = Cp, Ind, Flu) and a variable bridge substitution pattern (R1, R2 = H, Ph, cyclopentyl, cyclohexyl) were prepared starting from the corresponding epoxides. The solid state structures of six organic intermediates are reported in order to prove the stereochemistry of the ligand forming reactions. Treatment of the dilithio salts of 5a–d with ZrCl4 in CH2Cl2 afforded chiral ansa-zirconocene dichlorides (6a–d).

KW - Biscyclopentadienes

KW - Chiral Epoxides

KW - Chiral ansa-Zirconocene Dichlorides

KW - Fluorenyl Alcohols

KW - Spirocyclopropanes

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U2 - 10.1515/znb-1994-0404

DO - 10.1515/znb-1994-0404

M3 - Article

AN - SCOPUS:21344476344

SN - 0932-0776

VL - 49

SP - 451

EP - 458

JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

JF - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

IS - 4

ER -

Synthesis of Ethylene Bridged Biscyclopentadiene Ligand Precursor Compounds and Some of their ansa-Zirconocene Derivatives Chiral Epoxides: A Synthetic Strategy of High Variability

Abstract

Keywords

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