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Mechanism of the Deprotonation Reaction of Alkyl Benzyl Ethers with n ‐Butyllithium
Author(s) -
Raposo M. Luz,
FernándezNieto Fernando,
GarciaRio Luis,
RodríguezDafonte P.,
Paleo M. Rita,
Sardina F. Javier
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201204467
Subject(s) - deprotonation , chemistry , reactivity (psychology) , dimer , alkyl , ether , lithium (medication) , medicinal chemistry , butyllithium , oxygen atom , ion , organic chemistry , molecule , medicine , alternative medicine , pathology , endocrinology
Kinetic study of the α‐lithiation of benzyl methyl ether (BME) by n BuLi 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 n BuLi 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.
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