1310708-54-3Relevant articles and documents
Divergent reactivity of homologue ortho-Allenylbenzaldehydes controlled by the tether length: Chromone versus chromene formation
Alcaide, Benito,Almendros, Pedro,Fernndez, Israel,Del Campo, Teresa Martnez,Naranjo, Teresa
supporting information, p. 1533 - 1541 (2015/01/30)
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.
Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles
Wipf, Peter,Manojlovic, Marija D.
supporting information; experimental part, p. 824 - 830 (2011/08/10)
The one-pot hydrozirconation of allenes and nitriles followed by an in situ transmetalation of the allylzirconocene with dimethylzinc or zinc chloride provides functionalized homoallylic amines. An intramolecular version of this process leads to 3-aminote