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Issue 8, 2001
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Reactions of amides with organoaluminium: a useful synthetic route to aluminium diketiminates

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Abstract

The reaction of N-tert-butylbenzamide (tBuNHCOPh) with 1.1 molar equivalents of Me3Al in refluxing hexane afforded a five-coordinated dimeric compound [Me2Al{η2-tBuNC(Ph)(μ-O)}]21, whereas 2.2 molar equivalents yielded a monomeric compound [Me2Al{η2-tBuNCPh(μ-O)}AlMe3] 2. Reaction of PhCONHAr with 1 molar equivalent of Me3Al in toluene at 25 °C, gave four-coordinated dimeric eight-membered ring compounds [Me2Al{μ-η2-(p-XC6H4)NC(Ph)O}]2 (X = OMe 3 or  4). Benzanilide (PhNHCOPh) with 1.2 molar equivalents of Me3Al in refluxing toluene resulted in aluminium amidate 4 and a trace amount of an aluminium diketiminate, [Me2Al{η2-PhNC(Ph)C(H)C(Ph)NPh}] 5. Furthermore, PhCONHC6H4X-p reacts with 2 molar equivalents of R3Al in refluxing toluene affording aluminium diketiminate compounds, [R2Al{η2-(p-XC6H4)NC(Ph)C(R′)C(Ph)N(p-XC6H4)}] (R = Et, R′ = Me, X = H 6; R = Et, R′ = Me, X = Cl 7; R = Me, R′ = H, X = Cl 8; R = Me, R′ = H, X = Me 9; R = Et, R′ = Me, X = Me 10). Thus, this process offers a readily available synthetic route to the preparation of aluminium diketiminates which is otherwise difficult with aromatic substituents.

Graphical abstract: Reactions of amides with organoaluminium: a useful synthetic route to aluminium diketiminates [ ]

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Supplementary files

Article information


Submitted
13 Nov 2000
Accepted
14 Feb 2001
First published
27 Mar 2001

J. Chem. Soc., Dalton Trans., 2001, 1359-1365
Article type
Paper

Reactions of amides with organoaluminium: a useful synthetic route to aluminium diketiminates

Y. Huang, B. Huang, B. Ko and C. Lin, J. Chem. Soc., Dalton Trans., 2001, 1359
DOI: 10.1039/B009070K

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