An Azide-Free Synthesis of Metallodiazomethanes Using Nitrous Oxide
Robert J. Ward,
Mike Jörges,
Henning Remm
et al.
Abstract:Diazo compounds are valuable reagents in synthesis but usually require the use of potentially explosive or toxic starting materials. Here, we report the synthesis and isolation of alkali metal diazomethanides by the reaction of metalated ylides with nitrous oxide, resulting in a formal exchange of the phosphine ligand by dinitrogen. The reaction proceeds through a Wittig-like mechanism via a [3 + 2] cycloaddition of N 2 O across the ylide bond with release of phosphine oxide. The metalated diazomethanes exhibi… Show more
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