1972
DOI: 10.1002/prac.19723140121
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Dehydrierung von Ketonen mit Palladium(II)‐Verbindungen

Abstract: Cyclohexanon reagiert mit Palladium(II)‐Verbindungen in einer stöchiometrischen Reaktion unter Dehydrierung zum Cyclohexen‐(2)‐on. Diese Dehydrierungsreaktion ist allgemein auf Ketone anwendbar. Der Mechanismus der Reaktion wird diskutiert.

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Cited by 46 publications
(5 citation statements)
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“…These dehydrobrominations usually require quite vigorous conditions.1 This note reports our attempts to develop a mild method for this type of elimination using palladium tetrakis(triphenylphosphine) , 2 It was hoped that Pd(PPh3)4 would undergo facile oxidative addition with «-bromo ketones just as Pd(0) complexes do with other organic halides.3 The resulting species, for which one possible representation is shown in eq l,4•5 might be expected to expel a ß hydrogen along with palladium to form enone.® Presumably, the intermediate(s) involved would be similar to those in the direct oxidation of ketones to enones using Pd(II) salts. [7][8][9] The proposed method offers the potential advantage of regioselectivity in enone formation and could, in principle, be catalytic in palladium without added Cu(II) salts. 7•9 The method works well in the case of 2-bromo-l-tetralones, where the initially formed enone can aromatize simply by tautomerization.…”
Section: References and Notesmentioning
confidence: 99%
“…These dehydrobrominations usually require quite vigorous conditions.1 This note reports our attempts to develop a mild method for this type of elimination using palladium tetrakis(triphenylphosphine) , 2 It was hoped that Pd(PPh3)4 would undergo facile oxidative addition with «-bromo ketones just as Pd(0) complexes do with other organic halides.3 The resulting species, for which one possible representation is shown in eq l,4•5 might be expected to expel a ß hydrogen along with palladium to form enone.® Presumably, the intermediate(s) involved would be similar to those in the direct oxidation of ketones to enones using Pd(II) salts. [7][8][9] The proposed method offers the potential advantage of regioselectivity in enone formation and could, in principle, be catalytic in palladium without added Cu(II) salts. 7•9 The method works well in the case of 2-bromo-l-tetralones, where the initially formed enone can aromatize simply by tautomerization.…”
Section: References and Notesmentioning
confidence: 99%
“…Efforts were then focused toward the key aromatization step. Initial attempts to oxidize the silyl dienol ether of 7 and 8 with palladium 10 or MnO 2 11 saw competitive oxidation of the indenotetrahydropyridine core. Several other attempts to oxidize the dienolate or cyclohexenone directly also failed.…”
mentioning
confidence: 99%
“…The key intermediate 3 was obtained from commercially available citronellal 2 following a reported procedure. 3 The ketone 3 was exposed 4 to PdCl 2 in t-butanol containing 4 equivalent of Na 2 CO 3 at 80 °C to afford (-)-1 in 68%.…”
mentioning
confidence: 99%