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    Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10259/5532

    Título
    Experimental and Computational Study of the 1,5-O → N Carbamoyl Snieckus–Fries-Type Rearrangement
    Autor
    Feberero, ClaudiaUBU authority Orcid
    Sedano Labrador, CarlosUBU authority Orcid
    Suarez Pantiga, SamuelUBU authority Orcid
    Silva López, Carlos
    Sanz Díez, RobertoUBU authority Orcid
    Publicado en
    The Journal of Organic Chemistry. 2020, V. 85, n. 19, p. 12561–12578
    Editorial
    American Chemical Society
    Fecha de publicación
    2020-10
    ISSN
    0022-3263
    DOI
    10.1021/acs.joc.0c01732
    Abstract
    The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C−N multiple bond electrophiles have been thoroughly studied. A 1,5-O → N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O → N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized Oarylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.
    Palabras clave
    Aromatic compounds
    Organic compounds
    Rearrangement
    Reaction products
    Genetics
    Materia
    Química orgánica
    Chemistry, Organic
    URI
    http://hdl.handle.net/10259/5532
    Versión del editor
    https://doi.org/10.1021/acs.joc.0c01732
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    • Artículos SINTORG
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