Pérez Ruiz, R.; Sáez Cases, JA.; Domingo, LR.; Jiménez Molero, MC.; Miranda Alonso, MÁ. (2012). Ring splitting of azetidin-2-ones via radical anions. Organic and Biomolecular Chemistry. 10(39):7928-7932. https://doi.org/10.1039/c2ob26528a
Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/61121
Título:
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Ring splitting of azetidin-2-ones via radical anions
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Autor:
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Pérez Ruiz, Raúl
Sáez Cases, José Antonio
Domingo, Luis R.
Jiménez Molero, María Consuelo
Miranda Alonso, Miguel Ángel
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Entidad UPV:
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Universitat Politècnica de València. Departamento de Química - Departament de Química
Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química
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Fecha difusión:
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Resumen:
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The radical anions of azetidin-2-ones, generated by UV-irradiation in the presence of triethylamine, undergo ring-splitting via N-C4 or C3-C4 bond breaking, leading to open-chain amides. This reactivity diverges from that ...[+]
The radical anions of azetidin-2-ones, generated by UV-irradiation in the presence of triethylamine, undergo ring-splitting via N-C4 or C3-C4 bond breaking, leading to open-chain amides. This reactivity diverges from that found for the neutral excited states, which is characterised by alpha-cleavage. The preference for beta-cleavage is supported by DFT theoretical calculations on the energy barriers associated with the involved transition states. Thus, injection of one electron into the azetidin-2-one moiety constitutes a complementary activation strategy which may be exploited to produce new chemistry.
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Palabras clave:
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POLARIZABLE CONTINUUM MODEL
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BETA-LACTAM RING
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N-(ARYLIDENE(OR ALKYLIDENE)AMINO)-2-AZETIDINONES
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STEREOCONTROLLED SYNTHESIS
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STEREOSELECTIVE-SYNTHESIS
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PHOTOCHEMICAL-REACTIONS
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BUILDING-BLOCKS
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DNA PHOTOLYASE
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VINYL ETHERS
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AZETIDINES
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Derechos de uso:
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Reserva de todos los derechos
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Fuente:
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Organic and Biomolecular Chemistry. (issn:
1477-0520
) (eissn:
1477-0539
)
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DOI:
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10.1039/c2ob26528a
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Editorial:
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Royal Society of Chemistry
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Versión del editor:
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http://dx.doi.org/10.1039/c2ob26528a
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Código del Proyecto:
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info:eu-repo/grantAgreement/MICINN//JCI-2010-06204/ES/JCI-2010-06204/ /
...[+]
info:eu-repo/grantAgreement/MICINN//JCI-2010-06204/ES/JCI-2010-06204/ /
info:eu-repo/grantAgreement/GVA//PROMETEO08%2F2008%2F090/ES/Especies fotoactivas como sondas para proteínas/
info:eu-repo/grantAgreement/CSIC//JAEDOC 101-2011/
info:eu-repo/grantAgreement/UPV//20100994/
info:eu-repo/grantAgreement/MICINN//CTQ2010-14882/ES/DIADAS FOTOACTIVAS COMO SONDAS PARA LA GENERACION DE ESPECIES TRANSITORIAS EN SISTEMAS MICROHETEROGENEOS DE TIPO BIOMIMETICO/ /
info:eu-repo/grantAgreement/MICINN//CTQ2009-13699/ES/CTQ2009-13699/
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Agradecimientos:
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Financial support from the MICINN (Grants CTQ-2010-14882, CTQ-2009-13699 and JCI-2010-06204), Generalitat Valenciana (Prometeo 2008/90), from CSIC (JAEDOC 101-2011) and from the UPV (Grant No. 20100994 and MCI Program) is ...[+]
Financial support from the MICINN (Grants CTQ-2010-14882, CTQ-2009-13699 and JCI-2010-06204), Generalitat Valenciana (Prometeo 2008/90), from CSIC (JAEDOC 101-2011) and from the UPV (Grant No. 20100994 and MCI Program) is gratefully acknowledged.
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Tipo:
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Artículo
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