Double Friedel-Crafts Acylation Reactions on the Same Ring of a Metallocene: Synthesis of a 2 5-Diacetylphospharuthenocene - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2010

Double Friedel-Crafts Acylation Reactions on the Same Ring of a Metallocene: Synthesis of a 2 5-Diacetylphospharuthenocene

Résumé

The synthetic outcome of the Friedel–Crafts acylation of 1′,2′,3,3′,4,4′,5′-heptamethylphospharuthenocene reflects the nature of the acylating agent, with alkanoyl anhydride/trifluoromethanesulfonic acid (TfOH) reagents giving monosubstitution at the phospholyl ring, whereas alkanoyl chloride/AlCl3 gives 2,5-disubstitution. DFT calculations indicate that this unusual double acylation can be facilitated by the intervention of the phosphorus atom at an early stage in the reaction trajectory, with the acyl group being delivered from the phosphorus atom into the ring 2- or 2,5-positions.

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Catalyse

Dates et versions

hal-00577161 , version 1 (16-03-2011)

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Citer

Duncan Carmichael, Pascal Le Floch, X. F Le Goff, Olivier Piechaczyk, Nicolas Seeboth. Double Friedel-Crafts Acylation Reactions on the Same Ring of a Metallocene: Synthesis of a 2 5-Diacetylphospharuthenocene. Chemistry - A European Journal, 2010, 16, pp.14486-14497. ⟨10.1002/chem.200902409⟩. ⟨hal-00577161⟩
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