A Combined 1 H/ 6 Li NMR DOSY Strategy Finally Uncovers the Structure of Isopropyllithium in THF

Despite its common use in synthesis, the structure of isopropylliyhium in THF has never been determined, a dimer being generally proposed but not supported. This paper fills this data gap through a sophisticated NMR study that shows that, in THF at low-temperature, isopropyllithium is in the form of...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-09, Vol.23 (51), p.12475-12479
Main Authors: Barozzino-Consiglio, Gabriella, Hamdoun, Ghanem, Fressigné, Catherine, Harrison-Marchand, Anne, Maddaluno, Jacques, Oulyadi, Hassan
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary:Despite its common use in synthesis, the structure of isopropylliyhium in THF has never been determined, a dimer being generally proposed but not supported. This paper fills this data gap through a sophisticated NMR study that shows that, in THF at low-temperature, isopropyllithium is in the form of a 1:2 mixture of a trisolvated monomer and a disolvated dimer in equilibrium. The presence of the monomer, never evoked before, together with a hypo-solvation of the dimer hinted by DFT calculations, provides a rational explanation to the remarkable reactivity of this organolithium reagent in ethereal solvents.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201702990