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

Barozzino Consiglio, Gabriella;Hamdoun, Ghanem;Fressigné, Catherine;Harrison-Marchand, Anne;Oulyadi, Hassan;et.al.
(2017) Chemistry: A European Journal — Vol. 23, n° 51, p. 12475-12479 (2017)

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Abstract
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.
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Barozzino Consiglio, G., Hamdoun, G., Fressigné, C., Harrison-Marchand, A., Maddaluno, J., & Oulyadi, H. (2017). A Combined 1H/6Li NMR DOSY Strategy Finally Uncovers the Structure of Isopropyllithium in THF. Chemistry: A European Journal, 23(51), 12475-12479. https://doi.org/10.1002/chem.201702990 (Original work published 2017)