Efficient Approach to 1,2‐Diazepines via Formal Diazomethylene Insertion into the C—C Bond of Cyclobutenones.
2012
Efficient monocyclic 1,2-diazepine formation via a tandem electrocyclization reaction of cyclobutenones with lithiodiazoacetate is demonstrated. The reaction proceeds through an oxy anion-accelerated 4π-ring opening of cyclobutene followed by an 8π-ring closure of the resultant oxy anion-substituted diazo-diene under mild conditions to furnish a 1,2-diazepine via formal diazomethylene insertion into the C–C bond of cyclobutenone.
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