title: Mechanism of the deprotonation reaction of alkyl benzyl ethers with n-butyllithium.
abstract: Kinetic study of the α-lithiation of benzyl methyl ether (BME) by nBuLi has revealed that increasing the concentration of the organolithium compound does not necessarily increase the reactivity, and this is a consequence of the reactivities of the different nBuLi aggregates present in solution. We propose a dimer-based mechanism, in which a pre-complexation step is a key process for substrates bearing a donor oxygen atom that can interact with the lithium cation to form mixed dimers. For these studies, we have developed a system based on UV/Vis spectroscopy that allows kinetic measurements to be conducted at -80 °C under argon.
authors.affiliation: Departamento de Química Física, Centro de Investigación en Química Biológica y Materiales, Moleculares, Universidad de Santiago, 15782 Santiago, Spain.
authors.forename: M Luz
authors.initials: ML
authors.lastname: Raposo
authors.forename: Fernando
authors.initials: F
authors.lastname: Fernández-Nieto
authors.forename: Luis
authors.initials: L
authors.lastname: Garcia-Rio
authors.forename: P
authors.initials: P
authors.lastname: Rodríguez-Dafonte
authors.forename: M Rita
authors.initials: MR
authors.lastname: Paleo
authors.forename: F Javier
authors.initials: FJ
authors.lastname: Sardina
keywords: aggregation; butyllithium; deprotonation; kinetics; mechanism