Synthesis, Characterization, and Polymerization Properties of Bis(2-menthylindenyl)zirconium Dichloride and Bis(2-menthyl-4,7-dimethylindenyl)zirconium Dichloride
Ronald L. Halterman
1
,
Darryl R. Fahey*
1
,
Eric F Bailly
1
,
David W. Dockter
1
,
Oleg Stenzel
1
,
Jason L Shipman
1
,
MASOOD A. KHAN
1
,
Sebastian Dechert
1
,
Herbert Schumann
1
1
Department of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Norman, Oklahoma 73019, Research and Development, Phillips Petroleum Company, Bartlesville, Oklahoma 74004, and Institut für Anorganische und Analytische Chemie der Technischen Universität Berlin, Strasse des 17 Juni 135, D-10623 Berlin, Germany
|
Publication type: Journal Article
Publication date: 2000-11-10
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The tetrakis(triphenylphosphine)palladium-catalyzed cross coupling of 2-bromoindene or 2-bromo-4,7-dimethylindene with menthylmagnesium chloride gave the novel ligands 2-menthylindene (10) and 2-menthyl-4,7-dimethylindene (11) in 66 and 57% yields. These indenes were deprotonated with n-BuLi to give isolated indenyllithium complexes which were metalated with zirconium tetrachloride to give bis(2-menthylindenyl)zirconium dichloride (14) and bis(2-menthyl-4,7-dimethylindenyl)zirconium dichloride (15) in 40 and 66% yields. Both complexes formed as their single possible stereoisomer and were characterized by X-ray crystallography and MS, NMR, and IR spectroscopy. The variable-temperature 1H NMR spectrum of bis(2-menthyl-4,7-dimethylindenyl)zirconium dichloride (15) showed that it interconverts with a rotational activation barrier of about 12.5 ± 0.5 kcal/mol, and that a 60:40 mixture of C2-symmetric diastereomeric conformations was present at −50 °C. The 1H NMR spectrum of bis(2-menthylindenyl)zirconium dichl...
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Halterman R. L. et al. Synthesis, Characterization, and Polymerization Properties of Bis(2-menthylindenyl)zirconium Dichloride and Bis(2-menthyl-4,7-dimethylindenyl)zirconium Dichloride // Organometallics. 2000. Vol. 19. No. 25. pp. 5464-5470.
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Halterman R. L., Fahey* D. R., Bailly E. F., Dockter D. W., Stenzel O., Shipman J. L., KHAN M. A., Dechert S., Schumann H. Synthesis, Characterization, and Polymerization Properties of Bis(2-menthylindenyl)zirconium Dichloride and Bis(2-menthyl-4,7-dimethylindenyl)zirconium Dichloride // Organometallics. 2000. Vol. 19. No. 25. pp. 5464-5470.
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TY - JOUR
DO - 10.1021/om000551y
UR - https://doi.org/10.1021/om000551y
TI - Synthesis, Characterization, and Polymerization Properties of Bis(2-menthylindenyl)zirconium Dichloride and Bis(2-menthyl-4,7-dimethylindenyl)zirconium Dichloride
T2 - Organometallics
AU - Halterman, Ronald L.
AU - Fahey*, Darryl R.
AU - Bailly, Eric F
AU - Dockter, David W.
AU - Stenzel, Oleg
AU - Shipman, Jason L
AU - KHAN, MASOOD A.
AU - Dechert, Sebastian
AU - Schumann, Herbert
PY - 2000
DA - 2000/11/10
PB - American Chemical Society (ACS)
SP - 5464-5470
IS - 25
VL - 19
SN - 0276-7333
SN - 1520-6041
ER -
Cite this
BibTex (up to 50 authors)
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@article{2000_Halterman,
author = {Ronald L. Halterman and Darryl R. Fahey* and Eric F Bailly and David W. Dockter and Oleg Stenzel and Jason L Shipman and MASOOD A. KHAN and Sebastian Dechert and Herbert Schumann},
title = {Synthesis, Characterization, and Polymerization Properties of Bis(2-menthylindenyl)zirconium Dichloride and Bis(2-menthyl-4,7-dimethylindenyl)zirconium Dichloride},
journal = {Organometallics},
year = {2000},
volume = {19},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/om000551y},
number = {25},
pages = {5464--5470},
doi = {10.1021/om000551y}
}
Cite this
MLA
Copy
Halterman, Ronald L., et al. “Synthesis, Characterization, and Polymerization Properties of Bis(2-menthylindenyl)zirconium Dichloride and Bis(2-menthyl-4,7-dimethylindenyl)zirconium Dichloride.” Organometallics, vol. 19, no. 25, Nov. 2000, pp. 5464-5470. https://doi.org/10.1021/om000551y.