Article (Scientific journals)
Lithiation of toluene by organolithium compounds activated by lithium polyether alkoxides
Nugay, Nihan; Nugay, Turgut; Jérôme, Robert et al.
2002In Journal of Molecular Catalysis A: Chemical, 179 (1-2), p. 59-64
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Abstract :
[en] The catalytic effect of polyether alkoxides (PEAs) on the activity of organolithium. compounds as metallating agent has been investigated. Toluene has been lithiated by using different organolithiums activated by various PEAs. It has been found that n-BuLi, yields higher conversion with 100% benzylic position metallation, whereas sec-BuLi gives some metallation at ring positions with the most reactive ligand, lithium 2-methoxy ethoxide (LiOEM). Optimum PEA to organolithium molar ratio for both sec- and n-BuLi activated by LiOEM where the amount of toluene being kept constant, was found to be as 3:1 with highest yield and regioselectivity. Substantial increment in yield was observed when the amount of substrate increased whereas regioselectivity stayed almost constant. It was also found that, for a constant reactant molar ratio (3:1:15) for which the optimum results were achieved, reaction began early and then yield values increased with time whereas upon increase in reaction temperature from -78 to 20degreesC, the benzylic metallation yield increased drastically while keeping the same regioselectivity high.
Research center :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Materials science & engineering
Chemistry
Author, co-author :
Nugay, Nihan;  Bogazici University, Istanbul, Turkey > Department of Chemistry > Polymer Research Centre
Nugay, Turgut;  Bogazici University, Istanbul, Turkey > Department of Chemistry > Polymer Research Centre
Jérôme, Robert ;  Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Teyssié, Philippe ;  Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Lithiation of toluene by organolithium compounds activated by lithium polyether alkoxides
Publication date :
18 February 2002
Journal title :
Journal of Molecular Catalysis A: Chemical
ISSN :
1381-1169
eISSN :
1873-314X
Publisher :
Elsevier Science Bv, Amsterdam, Netherlands
Volume :
179
Issue :
1-2
Pages :
59-64
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique
Commentary :
The authors acknowledge Journal of Molecular Catalysis A: Chemical (Elsevier) for allowing them to archive this paper.
Available on ORBi :
since 25 March 2009

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