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    Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10259/4279

    Título
    Exploring the Reactivity of α-Lithiated Aryl Benzyl Ethers: Inhibition of the [1,2]-Wittig Rearrangement and the Mechanistic Proposal Revisited
    Autor
    Velasco, Rocío
    Silva López, Carlos
    Nieto Faza, Olalla .
    Sanz Díez, Robertountranslated
    Publicado en
    Chemistry-a european journal. 2015, V. 22, n. 42, p. 15058–15068
    Editorial
    Wiley-VCH Verlag
    Fecha de publicación
    2016-10
    ISSN
    0947-6539
    Abstract
    By carefullycontrolling the reactiontemperature,treatment of aryl benzylethers with tBuLi selectivelyleadsto a-lithiation, generating stable organolithiums that can bedirectlytrapped with avariety of selected electro philes,before they can undergo the expected [1,2]-Wittigrear-rangement. This rearrangement has been deeplystudied,both experimentally and computationally,with aryl a-lithiat-ed benzyl ethers bearing different substituents at the arylring. The obtained resultssupport the competence of acon-certedanionic intramolecular addition/elimination sequenceand aradical dissociation/recombination sequence for ex-plaining the tendency of migrationfor aryl groups.Themore favored rearrangementsare found for substrates withelectron-poor aryl groups that favor the anionic pathway
    Palabras clave
    density functio nal calculations
    lithiation
    oxygenheterocycles
    reaction mechanisms
    Wittig rearrangement
    URI
    http://hdl.handle.net/10259/4279
    Versión del editor
    http://dx.doi.org/10.1002/chem.201602254
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    • Artículos SINTORG
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