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
Posted on 2018-07-13 - 00:00
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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Dai, Wen; Geib, Steven J.; Curran, Dennis P. (2018). 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. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.8b01125
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