In the May issue, an interesting Highlight on the synthetic uses of diethylaluminium azide (Et2AlN3) by Monticelli and Pace (Vienna) summarises the formation of tetrazoles and bis-tetrazoles from (di)nitriles, triazoles and beta-azidoketones (by Michael addition) from alpha-beta unsaturated ketones, beta-azidoalcohols from the ring opening of epoxides, which effectively corresponds to the addition of HO-N3 to C=C double bonds. Numerous other reactions are also described, including the formation of acyl azides from esters (by substitution) and of azido-functionalised C_(60) (by addition). The reactivity of this reagent arises from a combination of the Lewis acid nature of Al and the nucleophilic and. cycloaddition properties of the azide group.
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