volume 51 issue 15 pages 4541-4550

The mechanism of the zirconium catalysed ethyl- and 2-magnesioethyl-magnesiation of unactivated alkenes

Dorian P Lewis 1
Raymond V H Jones 2
2
 
ZENECA Fine Chemicals Manufacturing Organisation, Grangemouth, Stirlingshire, FK3 8XG, U.K.
Publication typeJournal Article
Publication date1995-04-01
scimago Q3
wos Q2
SJR0.426
CiteScore4.1
Impact factor2.2
ISSN00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Deuterium labelling experiments prove that the zirconocene dichloride catalysed ethylmagnesiation of alkenes occurs via a zirconocene η2-ethylene complex and allow a deuterium isotope effect for a key β-hydride transfer to be estimated ( k H k D = 2.5 ). Transmetallation from zirconium to magnesium to form 1,4-dimagnesiated reagents is shown to be an intramolecular process. Kinetic studies show that the reaction between η2-ethylene zirconocene and the alkene is rate limiting and that Lewis bases inhibit the reaction by decreasing the amount of η2-ethylene zirconocene in equilibrium with the ‘ate’ complex [Cp2Zr(CH2=CH2)Et]−.[MgX.Base]+.
Found 
Found 

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GOST Copy
Lewis D. P. et al. The mechanism of the zirconium catalysed ethyl- and 2-magnesioethyl-magnesiation of unactivated alkenes // Tetrahedron. 1995. Vol. 51. No. 15. pp. 4541-4550.
GOST all authors (up to 50) Copy
Lewis D. P., Whitby R. J., Jones R. V. H. The mechanism of the zirconium catalysed ethyl- and 2-magnesioethyl-magnesiation of unactivated alkenes // Tetrahedron. 1995. Vol. 51. No. 15. pp. 4541-4550.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/0040-4020(94)01139-Q
UR - https://doi.org/10.1016/0040-4020(94)01139-Q
TI - The mechanism of the zirconium catalysed ethyl- and 2-magnesioethyl-magnesiation of unactivated alkenes
T2 - Tetrahedron
AU - Lewis, Dorian P
AU - Whitby, Richard J.
AU - Jones, Raymond V H
PY - 1995
DA - 1995/04/01
PB - Elsevier
SP - 4541-4550
IS - 15
VL - 51
SN - 0040-4020
SN - 1464-5416
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{1995_Lewis,
author = {Dorian P Lewis and Richard J. Whitby and Raymond V H Jones},
title = {The mechanism of the zirconium catalysed ethyl- and 2-magnesioethyl-magnesiation of unactivated alkenes},
journal = {Tetrahedron},
year = {1995},
volume = {51},
publisher = {Elsevier},
month = {apr},
url = {https://doi.org/10.1016/0040-4020(94)01139-Q},
number = {15},
pages = {4541--4550},
doi = {10.1016/0040-4020(94)01139-Q}
}
MLA
Cite this
MLA Copy
Lewis, Dorian P., et al. “The mechanism of the zirconium catalysed ethyl- and 2-magnesioethyl-magnesiation of unactivated alkenes.” Tetrahedron, vol. 51, no. 15, Apr. 1995, pp. 4541-4550. https://doi.org/10.1016/0040-4020(94)01139-Q.