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

AuthorsAlcaide, Benito ; Almendros, Pedro ; Fernández, I.; Campo, T. M. del; Naranjo, T.
Issue Date2015
PublisherJohn Wiley & Sons
CitationChemistry - A European Journal 21: 1533-1541 (2015)
AbstractThe 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.
Identifiersdoi: 10.1002/chem.201404516
issn: 0947-6539
e-issn: 1521-3765
Appears in Collections:(IQOG) Artículos
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