English   español  
Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/110048
Compartir / Impacto:
Estadísticas
Add this article to your Mendeley library MendeleyBASE
Citado 7 veces en Web of Knowledge®  |  Pub MebCentral Ver citas en PubMed Central  |  Ver citas en Google académico
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar otros formatos: Exportar EndNote (RIS)Exportar EndNote (RIS)Exportar EndNote (RIS)
Título

Divergent reactivity of homologue ortho-Allenylbenzaldehydes controlled by the tether length: Chromone versus chromene formation

Autor Alcaide, Benito ; Almendros, Pedro ; Fernández, I.; Campo, T. M. del; Naranjo, T.
Fecha de publicación 2015
EditorJohn Wiley & Sons
Citación Chemistry - A European Journal 21: 1533-1541 (2015)
ResumenThe divergent behavior of two homologue allenals, namely, 2-(buta-2,3-dienyloxy)- and 2-(propa-1,2-dienyloxy)benzaldehydes, as cyclization substrates is described. 2-(Buta-2,3-dienyloxy)benzaldehydes suffers a formal allenic carbocyclization reaction to afford chromenes, whereas 2-(propa-1,2-dienyloxy)benzaldehydes react to yield chromones. The formation of chromenes is strictly a formal hydroarylation process divided into two parts, namely, allenic Claisen-type rearrangement and oxycyclization. An unknown N-heterocyclic carbene (NHC)-catalyzed allenic hydroacylation reaction must be invoked to account for the preparation of chromones. ortho-Allenylbenzaldehydes bearing either electron-donating substituents or electron-withdrawing substituents worked well to afford both the hydroarylation and hydroacylation products. This unexpected difference in reactivity can be rationalized by means of density functional theory calculations.
URI http://hdl.handle.net/10261/110048
DOI10.1002/chem.201404516
Identificadoresdoi: 10.1002/chem.201404516
issn: 0947-6539
e-issn: 1521-3765
Aparece en las colecciones: (IQOG) Artículos
Ficheros en este ítem:
Fichero Descripción Tamaño Formato  
accesoRestringido.pdf15,38 kBAdobe PDFVista previa
Visualizar/Abrir
Mostrar el registro completo
 



NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.