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Reactions of N-Heterocyclic Carbene Boranes with 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione: Synthesis of Mono- and Bis-hydrazonyl NHC-Boranes



Reactions of N-Heterocyclic Carbene Boranes with 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione: Synthesis of Mono- and Bis-hydrazonyl NHC-Boranes



Journal of Organic Chemistry 83(15): 8775-8779



N-Heterocyclic carbene boranes (NHC-boranes) react with 5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dione at 40 °C in dichloromethane to provide NHC-boryl hydrazone derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione. These hydrazones disproportionate to bis-hydrazones on treatment with diiodine in dichloromethane at room temperature. The mono- and bis-hydrazones are yellow solids that are stable to chromatography and storage.

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Accession: 065460573

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PMID: 30004702

DOI: 10.1021/acs.joc.8b01125


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