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A Novel Catalytic Route to Polymerizable Bicyclic Cyclic Carbonate Monomers from Carbon Dioxide

  • Datos identificativos

    Identificador: imarina:9262313
    Autores:
    Qiao CShi WBrandolese ABenet-Buchholz JEscudero-Adán ECKleij AW
    Resumen:
    A new catalytic route has been developed for the coupling of epoxides and CO2 affording polymerizable six-membered bicyclic carbonates. Cyclic epoxides equipped with a beta-positioned OH group can be transformed into structurally diverse bicyclic cyclic carbonates in good yields and with high selectivity. Key to the chemo-selectivity is the difference between the reactivity of syn- and anti-configured epoxy alcohols, with the latter leading to six-membered ring carbonate formation in the presence of a binary Al-III aminotriphenolate complex/DIPEA catalyst. X-ray analyses show that the conversion of the syn-configured substrate evolves via a standard double inversion pathway providing a five-membered carbonate product, whereas the anti-isomer allows for activation of the oxirane unit of the substrate opposite to the pendent alcohol. The potential use of these bicyclic products is shown in ring-opening polymerization offering access to rigid polycarbonates with improved thermal resistance.
  • Otros:

    Autor según el artículo: Qiao C; Shi W; Brandolese A; Benet-Buchholz J; Escudero-Adán EC; Kleij AW
    Departamento: Química Física i Inorgànica
    Autor/es de la URV: Benet Buchholz, Jordi / Qiao, Chang
    Palabras clave: Carbon dioxide Carbonylation Chemicals Co2 Conversion Cyclic carbonates Diols Epoxides Homogeneous catalysis Monomers Pressure Ring-opening polymerization Strategies Transformation
    Resumen: A new catalytic route has been developed for the coupling of epoxides and CO2 affording polymerizable six-membered bicyclic carbonates. Cyclic epoxides equipped with a beta-positioned OH group can be transformed into structurally diverse bicyclic cyclic carbonates in good yields and with high selectivity. Key to the chemo-selectivity is the difference between the reactivity of syn- and anti-configured epoxy alcohols, with the latter leading to six-membered ring carbonate formation in the presence of a binary Al-III aminotriphenolate complex/DIPEA catalyst. X-ray analyses show that the conversion of the syn-configured substrate evolves via a standard double inversion pathway providing a five-membered carbonate product, whereas the anti-isomer allows for activation of the oxirane unit of the substrate opposite to the pendent alcohol. The potential use of these bicyclic products is shown in ring-opening polymerization offering access to rigid polycarbonates with improved thermal resistance.
    Áreas temáticas: Astronomia / física Catalysis Chemistry Chemistry (all) Chemistry (miscellaneous) Chemistry, multidisciplinary Ciências biológicas i Ciências biológicas ii Ciências biológicas iii Engenharias ii Farmacia General chemistry General medicine Interdisciplinar Materiais Medicina i Medicina ii Química
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    Direcció de correo del autor: chang.qiao@estudiants.urv.cat
    Fecha de alta del registro: 2024-09-07
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    Referencia al articulo segun fuente origial: Angewandte Chemie (International Ed. Print). 61 (27): e202205053-e202205053
    Referencia de l'ítem segons les normes APA: Qiao C; Shi W; Brandolese A; Benet-Buchholz J; Escudero-Adán EC; Kleij AW (2022). A Novel Catalytic Route to Polymerizable Bicyclic Cyclic Carbonate Monomers from Carbon Dioxide. Angewandte Chemie (International Ed. Print), 61(27), e202205053-e202205053. DOI: 10.1002/anie.202205053
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2022
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary
    Carbon dioxide
    Carbonylation
    Chemicals
    Co2
    Conversion
    Cyclic carbonates
    Diols
    Epoxides
    Homogeneous catalysis
    Monomers
    Pressure
    Ring-opening polymerization
    Strategies
    Transformation
    Astronomia / física
    Catalysis
    Chemistry
    Chemistry (all)
    Chemistry (miscellaneous)
    Chemistry, multidisciplinary
    Ciências biológicas i
    Ciências biológicas ii
    Ciências biológicas iii
    Engenharias ii
    Farmacia
    General chemistry
    General medicine
    Interdisciplinar
    Materiais
    Medicina i
    Medicina ii
    Química
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