A Combined 1 H/ 6 Li NMR DOSY Strategy Finally Uncovers the Structure of Isopropyllithium in THF - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2017

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

Résumé

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.

Domaines

Chimie organique
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Dates et versions

hal-02019154 , version 1 (14-02-2019)

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Gabriella Barozzino-Consiglio, Ghanem Hamdoun, Catherine Fressigné, Anne Harrison-Marchand, Jacques Maddaluno, et al.. A Combined 1 H/ 6 Li NMR DOSY Strategy Finally Uncovers the Structure of Isopropyllithium in THF. Chemistry - A European Journal, 2017, 23 (51), pp.12475-12479. ⟨10.1002/chem.201702990⟩. ⟨hal-02019154⟩
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