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Título: | Divergent reactivity of homologue ortho-Allenylbenzaldehydes controlled by the tether length: Chromone versus chromene formation |
Autor: | Alcaide, Benito CSIC ORCID; Almendros, Pedro CSIC ORCID ; Fernández, I. CSIC ORCID; Campo, T. M. del; Naranjo, T. | Fecha de publicación: | 2015 | Editor: | John Wiley & Sons | Citación: | Chemistry - A European Journal 21: 1533-1541 (2015) | Resumen: | The 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 | DOI: | 10.1002/chem.201404516 | Identificadores: | doi: 10.1002/chem.201404516 issn: 0947-6539 e-issn: 1521-3765 |
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